4-(hydroxymethyl)benzaldehyde diethyl acetal
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran for 1h; | 100% |
sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In water at 30℃; for 0.0833333h; | 96% |
With hydrogenchloride In diethyl ether at 25℃; for 1h; Yield given; |
4-(hydroxymethyl)benzaldehyde dimethyl acetal
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With sulfuric acid; water In tetrahydrofuran at 20℃; for 3h; | 100% |
With sulfuric acid In tetrahydrofuran at 20℃; for 2h; |
4-Carboxybenzaldehyde
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With samarium diiodide; water; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol at 20℃; for 0.1h; Reduction; | 95% |
(+/-)-4-(3,4,5,6-tetrahydro-2H-pyran-2-yloxymethyl)benzaldehyde
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With zinc(II) trifluoromethanesulfonate In methanol at 20℃; for 0.5h; | 95% |
4-(diethylaminocarbonyl)benzoic acid
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-(diethylaminocarbonyl)benzoic acid With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: With zirconocene dichloride In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere; | 93% |
4-(hydroxymethyl)benzyl chloride
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃; for 6h; Reflux; | 93% |
terephthalaldehyde,
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With formic acid; [(η5-C5H5)Ru(κ1-P-PPh2Py)(PPh3)Cl]; sodium hydroxide In water; acetonitrile at 80℃; for 8h; | 92% |
With bis(η5-cyclopentadienyl)hafnium dihydride In isopropyl alcohol at 80℃; for 8h; | 91% |
With sodium tetrahydroborate In ethanol at 0℃; for 1h; | 91% |
p-xylylene glycol
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With oxygen In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 24h; Irradiation; | 90% |
With sodium tetrahydroborate In tetrahydrofuran; ethanol at 0 - 2℃; | 88.9% |
With dihydrogen peroxide In neat (no solvent) at 70℃; for 7h; Green chemistry; chemoselective reaction; | 70% |
methyl 4-formylbenzoate
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: methyl 4-formylbenzoate With trimethylaluminum; isopropylmagnesium chloride; N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; for 2h; Stage #2: With diisobutylaluminium hydride In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; for 0.5h; | 89% |
Stage #1: methyl 4-formylbenzoate With trimethylaluminum; isopropylmagnesium chloride; N,O-dimethylhydroxylamine*hydrochloride Stage #2: With diisobutylaluminium hydride Stage #3: With water chemoselective reaction; | 89% |
Stage #1: methyl 4-formylbenzoate With trimethylsilyl trifluoromethanesulfonate; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 8h; Inert atmosphere; Stage #3: With water; sodium hydrogencarbonate In methanol; hexane; dichloromethane at 40℃; for 2h; chemoselective reaction; | 80% |
4-((tert-butyldimethylsilyloxy)methyl)benzaldehyde
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With 1,11-bis(3-methyl-3H-imidazolium-1-yl)-3,6,9-trioxaundecane di(methanesulfonate) In methanol at 20℃; for 1.33333h; | 89% |
4-Methylbenzyl alcohol
A
4-methyl-benzaldehyde
B
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; Montmorillonite K10; silver nitrate In hexane at 60℃; for 2.5h; | A 86% B 6 % Chromat. |
terephthalaldehyde,
A
p-xylylene glycol
B
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With C48H43ClN2P2Ru; ammonium formate In water; toluene at 90℃; for 9h; Catalytic behavior; Schlenk technique; | A 17% B 83% |
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature; | A 3% B 74% |
With Grubbs catalyst first generation; potassium hydroxide In 1,4-dioxane at 80℃; for 20h; Cannizzaro reaction; | A 36% B 40% |
terephthalaldehyde mono(diethylacetal)
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: terephthalaldehyde mono(diethylacetal) With lithium aluminium tetrahydride In diethyl ether for 2h; Reduction; Heating; Stage #2: With hydrogenchloride In diethyl ether; water for 0.0333333h; Hydrolysis; | 78% |
Multi-step reaction with 2 steps 1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1 h / 0 °C 2: HCl / diethyl ether / 1 h / 25 °C View Scheme | |
Stage #1: terephthalaldehyde mono(diethylacetal) With sodium tetrahydroborate In methanol for 3h; Stage #2: With hydrogenchloride; methanol; water at 0 - 20℃; for 24h; |
(2-aminomethylpyridine)
terephthalaldehyde,
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With hydrogen; palladium on activated carbon In methanol | 78% |
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; water for 48h; Ambient temperature; | 77% |
2-(4-hydroxymethylphenyl)-1,3-dithiane
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With p-benzoquinone; sodium iodide In water; acetonitrile at 100℃; for 48h; | 73% |
4-Carboxybenzaldehyde
A
p-xylylene glycol
B
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With phenylsilane; C34H30CoO6; potassium In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; Schlenk technique; Glovebox; | A n/a B 73% |
p-xylylene glycol
A
terephthalaldehyde,
B
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With manganese(IV) oxide; oxygen In toluene at 110℃; for 8h; Green chemistry; | A 62% B 36% |
With cucurbit[8]uril; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water for 0.25h; Catalytic behavior; Reagent/catalyst; Temperature; Reflux; | A 37% B 44% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [Cu([bis(3-tert-butyl-2-hydroxybenzyl)](2-pyridylmethyl)amine)(acetate)(acetic acid)]; potassium carbonate In water at 25℃; for 24h; Catalytic behavior; | A 37 %Chromat. B 16% |
(4-vinyl-phenyl)-methanol
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: (4-vinyl-phenyl)-methanol With sodium periodate; C20H20ClN6Ru(1+)*Cl(1-) In water; acetone at 20℃; for 1.41667h; Stage #2: With sodium sulfite In dichloromethane; water for 0.166667h; Catalytic behavior; | 55% |
4-chloromethylbenzaldehyde
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With barium dihydroxide |
p-Xylylene dichloride
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With ethanol; nitric acid; silver nitrate | |
With methanol; sodium nitrate |
7,8-dioxabicyclo<4.2.2>deca-2,4,9-triene
A
terephthalaldehyde,
B
benzaldehyde
C
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
In acetonitrile at 130℃; Yield given. Yields of byproduct given; | |
In acetonitrile at 130℃; Yield given; |
4-(1',3'-dioxolan-2'-yl)benzyl alcohol
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at 25℃; for 6h; | |
Acid hydrolysis; | |
With hydrogenchloride In methanol at 30℃; for 1h; |
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With water | |
With sodium carbonate |
2-bromo-2-methylpropionic acid methyl ester
p-xylylene glycol
A
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Multistep reaction; |
5-(2-methylpropane-1-sulfonyl)-1-phenyl-1H-tetrazole
4-(hydroxymethyl)benzaldehyde dimethyl acetal
C
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Multistep reaction. Title compound not separated from byproducts; |
methyl 4-(1,3-dioxolan-2-yl)benzoate
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithiumaluminium hydride / tetrahydrofuran 2: Acid hydrolysis View Scheme | |
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / 1 h / 0 °C 2: 3M aq. HCl / tetrahydrofuran / 6 h / 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C 2: hydrogenchloride / methanol / 1 h / 30 °C View Scheme |
4-cyanobenzyl chloride
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: SnCl2; HCl; diethyl ether / anschl. mit H2O 2: aqueous Ba(OH)2 View Scheme |
terephthalaldehyde mono(diethylacetal)
trifluoroacetic acid
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With sodium borohydrid In methanol; chloroform; ethyl acetate | |
With sodium tetrahydroborate In methanol; chloroform |
Conditions | Yield |
---|---|
With triethylamine In ethanol at 50℃; | 100% |
1.3-propanedithiol
4-(hydroxylmethyl)benzaldehyde
2-(4-hydroxymethylphenyl)-1,3-dithiane
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane for 0.5h; Inert atmosphere; Schlenk technique; | 100% |
With copper(II) sulfate In dichloromethane at 20℃; |
tert-butylchlorodiphenylsilane
4-(hydroxylmethyl)benzaldehyde
4-({[tert-butyl(diphenyl)silyl]oxy}methyl)benzaldehyde
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 1.25h; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
With sodium sulfate In dichloromethane at 20℃; for 3h; | 99% |
tert-butyldimethylsilyl chloride
4-(hydroxylmethyl)benzaldehyde
4-((tert-butyldimethylsilyloxy)methyl)benzaldehyde
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 1h; Inert atmosphere; | 98% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere; | 87% |
Stage #1: 4-(hydroxylmethyl)benzaldehyde With 1H-imidazole In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 24h; Inert atmosphere; | 84% |
With 1H-imidazole In acetonitrile at 25℃; for 8h; Yield given; | |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
triethylsilane
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
AuCl(xanthphos) In 1,2-dichloro-ethane at 50℃; for 2h; | 98% |
4-(hydroxylmethyl)benzaldehyde
3-hydroxymethyl-benzoic acid
Conditions | Yield |
---|---|
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h; | 98% |
With NADH oxidase and 3-succinoylsemialdehyde-pyridine dehydrogenase co-expressed in Escherichia coli cells In aq. phosphate buffer at 30℃; for 3h; pH=7; Microbiological reaction; | 95% |
With C20H25N2(1+)*Cl(1-); water; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 16h; Schlenk technique; chemoselective reaction; | 85% |
3-bromo-2-chloroprop-1-ene
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With indium In tetrahydrofuran; water Ambient temperature; | 97% |
4-phenyl-4-vinyl-1,3-dioxolan -2-one
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With potassium phosphate; cobalt(II) chloride hexahydrate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 20℃; for 4h; Schlenk technique; Sealed tube; Inert atmosphere; Irradiation; diastereoselective reaction; | 97% |
C25H31NP(1+)*Cl(1-)
4-(hydroxylmethyl)benzaldehyde
trans-4-(N,N-diphenylamino)-4'-(hydroxymethyl)stilbene
Conditions | Yield |
---|---|
With lithium hydroxide In water at 80℃; for 4h; Wittig reaction; Inert atmosphere; stereoselective reaction; | 96% |
4-(hydroxylmethyl)benzaldehyde
4-(bromomethyl)benzaldehyde
Conditions | Yield |
---|---|
With hydrogen bromide In dichloromethane; acetic acid | 95% |
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 4h; | 95% |
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 10h; | 88% |
methanesulfonyl chloride
4-(hydroxylmethyl)benzaldehyde
4-formylbenzyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -5℃; for 0.25h; | 95% |
trifluoroacetic anhydride
4-(hydroxylmethyl)benzaldehyde
p-formylbenzyl trifluoroacetate
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 2h; Inert atmosphere; | 95% |
4-(hydroxylmethyl)benzaldehyde
p-xylylene glycol
Conditions | Yield |
---|---|
With formic acid; C20H29ClIrN4(1+)*Cl(1-) In water at 80℃; for 0.0833333h; | 95% |
With HNa*CHO2(1-); C63H72ClN3O5PRuS(1+)*Br(1-) In dimethylsulfoxide-d6; water-d2 at 37℃; for 12h; |
4-(hydroxylmethyl)benzaldehyde
4-((hydroxyimino)methyl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-(hydroxylmethyl)benzaldehyde With dihydrogen peroxide at 20℃; for 0.166667h; Green chemistry; Stage #2: With hydroxylamine hydrochloride for 4h; Catalytic behavior; Green chemistry; | 95% |
N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine; 4-(hydroxylmethyl)benzaldehyde In water at 20℃; for 24h; Stage #2: With lead dioxide In water for 2h; | 93% |
(trifluoromethyl)trimethylsilane
4-(hydroxylmethyl)benzaldehyde
1-(1-hydroxy-2,2,2-trifluoroethyl)-4-(hydroxymethyl)benzene
Conditions | Yield |
---|---|
Stage #1: (trifluoromethyl)trimethylsilane; 4-(hydroxylmethyl)benzaldehyde In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Sealed tube; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Sealed tube; Stage #3: With tetrabutyl ammonium fluoride; water In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Sealed tube; | 92% |
4-(hydroxylmethyl)benzaldehyde
terephthalaldehyde,
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nitromethane; oxygen; 1,10-ethyleneisoalloxazinium chloride at 40℃; for 14h; | 91% |
With 9-fluorenone In dimethyl sulfoxide at 20℃; Irradiation; | 90% |
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 50℃; for 30h; | 89% |
Conditions | Yield |
---|---|
In methanol for 2h; Reflux; | 91% |
para-methylacetophenone
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 0 - 20℃; for 24h; Aldol Condensation; | 90% |
With potassium hydroxide In ethanol; water Aldol Condensation; |
triisopropylsilyl chloride
4-(hydroxylmethyl)benzaldehyde
4-((triisopropylsilyloxy)methyl)benzaldehyde
Conditions | Yield |
---|---|
With 1H-imidazole; triethylamine In dichloromethane at 20℃; for 1h; | 90% |
Molecule structure of 4-(Hydroxymethyl)benzaldehyde (CAS NO.52010-97-6):
IUPAC Name: 4-(Hydroxymethyl)benzaldehyde
Molecular Weight: 136.14792 g/mol
Molecular Formula: C8H8O2
XLogP3: 0.8
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Exact Mass: 136.05243
MonoIsotopic Mass: 136.05243
Topological Polar Surface Area: 37.3
Heavy Atom Count: 10
Canonical SMILES: C1=CC(=CC=C1CO)C=O
InChI: InChI=1S/C8H8O2/c9-5-7-1-2-8(6-10)4-3-7/h1-5,10H,6H2
InChIKey: ZFHUHPNDGVGXMS-UHFFFAOYSA-N
Product Categories of 4-(Hydroxymethyl)benzaldehyde (CAS NO.52010-97-6): Organic Building Blocks
4-(Hydroxymethyl)benzaldehyde (CAS NO.52010-97-6) is also named as p-Tolualdehyde,a-hydroxy- (6CI,7CI) ; p-(Hydroxymethyl)benzaldehyde .
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