4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With water | 100% |
Conditions | Yield |
---|---|
With hydrogen In water at 70℃; Catalytic behavior; | A 99.9% B n/a |
With hydrogen In water at 20 - 100℃; under 3750.38 Torr; for 1h; Kinetics; Reagent/catalyst; Temperature; Pressure; Autoclave; | A 90.9% B 9.1% |
With 2 wt% Pd/C; hydrogen In water at 20 - 100℃; under 3750.38 Torr; for 1h; Kinetics; Reagent/catalyst; Autoclave; | A 21.8% B 78.3% |
Conditions | Yield |
---|---|
With whole cells of recombinant strain VA1 In aq. phosphate buffer at 30℃; for 24h; pH=7.4; Temperature; Microbiological reaction; | 99.2% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol for 1h; | 98% |
With aluminum oxide; zinc(II) tetrahydroborate In tetrahydrofuran at 20℃; for 0.08h; chemoselective reaction; | 97% |
With water; nickel dichloride; zinc In N,N-dimethyl-formamide for 2h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h; | 98% |
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane for 4h; Ambient temperature; | 73% |
With D-glucose In aq. phosphate buffer at 30℃; for 29h; pH=8; Enzymatic reaction; | 69% |
With hydrogen In aq. phosphate buffer at 50℃; under 3750.38 Torr; for 24h; pH=2; Autoclave; |
2-methoxy-4-((methoxymethoxy)methyl) phenol
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.025h; Microwave irradiation; chemoselective reaction; | 95% |
phosphotungstic acid In ethanol for 4h; Heating; | 81% |
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With silica gel In methanol at 60℃; for 3h; Inert atmosphere; | 95% |
3-methoxy-4-(2-propenyloxy) benzenemethanol
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With cerium(III) chloride; sodium iodide In acetonitrile for 6h; deallylation; Heating; | 94% |
4-((ethoxymethoxy)methyl)-2-methoxy phenol
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0333333h; Microwave irradiation; chemoselective reaction; | 93% |
phosphotungstic acid In ethanol for 3h; Heating; | 91% |
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.5h; | 90% |
vanillin
A
4-hydroxymethyl-2-methoxyphenol
B
2-methoxy-4-methoxymethylphenol
Conditions | Yield |
---|---|
In methanol for 0.0833333h; Ambient temperature; | A n/a B 60% |
(3,4-dimethoxyphenyl)methanol
A
3-hydroxy-4-methoxybenzyl alcohol
B
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611 In aq. buffer at 35℃; for 24h; pH=6.5; Inert atmosphere; Enzymatic reaction; regioselective reaction; | A 47% B 53% |
vanillin
A
p-cresol
B
2-Methoxy-4-methylphenol
C
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave; | A 6.9% B 52.3% C 6.63% |
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave; | A 6.9% B 52.9% C 6.9% |
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave; | A 5.3% B 49.9% C 11.8% |
Conditions | Yield |
---|---|
With ammonium chloride; magnesium at 20℃; for 3h; Irradiation; | A 8% B 51% |
With sodium amalgam; ethanol man neutralisiert das Reaktionsprodukt mit H2SO4, filtriert und schuettelt das Filtrat mit Aether aus; | |
With sodium amalgam; water | |
With sodium amalgam; ethanol |
Conditions | Yield |
---|---|
With Ximenia american In aq. phosphate buffer; water at 30℃; for 72h; pH=7; Enzymatic reaction; | A 51% B n/a |
With roots of Conium maculatum In water at 20℃; for 48h; Enzymatic reaction; | A 27 %Chromat. B 73 %Chromat. |
4-benzyloxy-3-methoxybenzyl alcohol
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With Mortierella isabellina NRRL 1757 Ambient temperature; | 40% |
Veratric acid
A
4-(hydroxymethyl)benzene-1,2-diol
B
4-hydroxymethyl-2-methoxyphenol
C
(3,4-dimethoxyphenyl)methanol
Conditions | Yield |
---|---|
With potassium hydroxide; samarium diiodide In tetrahydrofuran; water for 0.00194444h; Ambient temperature; | A 4% B 7% C 28% |
vanillin
A
4-hydroxymethyl-2-methoxyphenol
B
3-methoxy-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With Pseudomonas fluorescens B56 (IFO 12055) at 30℃; for 7h; Mechanism; growing conditions; | |
With sodium hydroxide; formaldehyd; silver | |
With sodium hydroxide; formaldehyd; silver |
Conditions | Yield |
---|---|
With sodium hydroxide | |
With sodium hydroxide |
piperonol
A
3-hydroxy-4-methoxybenzyl alcohol
B
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In toluene for 3h; Heating; Title compound not separated from byproducts; |
(+/-)-orientaline
A
1,2-didehydrocoripallinium ion
B
6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol
C
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With dihydrogen peroxide In methanol; water for 14h; Ambient temperature; ascorbate oxidase from Cucurbita pepo medullosa L., phosphate buffer pH 7.0; | A n/a B 29 mg C 43 mg D 62 mg |
With dihydrogen peroxide In methanol; water for 14h; Product distribution; Ambient temperature; ascorbate oxidase from Cucurbita pepo medullosa L. or peroxidase from Nelumbo nucifera Gaertn.; phosphate buffer pH 7.0; | A n/a B 29 mg C 43 mg D 62 mg |
Vanillylamin
A
4-hydroxymethyl-2-methoxyphenol
B
3-methoxy-4-hydroxybenzoic acid
C
vanillin
Conditions | Yield |
---|---|
With Pseudomonas fluorescens B56 (IFO 12055) at 30℃; for 7h; Mechanism; effect of growing and non-growing conditions, effect of reaction times; |
3-methoxybenzyl alcohol
A
2-hydroxy-3-methoxybenzyl alcohol
B
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
methyl 6-O-(4-hydroxy-3-methoxybenzyl)-α-D-glucopyranoside
A
4-hydroxymethyl-2-methoxyphenol
B
methyl-alpha-D-glucopyranoside
Conditions | Yield |
---|---|
With benzoquinone N-chloroimine; water at 60℃; Rate constant; pH 1.1; |
methyl 4-O-(4-hydroxy-3-methoxybenzyl)-α-D-glucopyranoside
A
4-hydroxymethyl-2-methoxyphenol
B
methyl-alpha-D-glucopyranoside
Conditions | Yield |
---|---|
With benzoquinone N-chloroimine; water at 60℃; Rate constant; pH 1.1; |
methanol
vanillin
A
4-hydroxymethyl-2-methoxyphenol
B
2-methoxy-4-methoxymethylphenol
Conditions | Yield |
---|---|
for 0.0833333h; Ambient temperature; |
Conditions | Yield |
---|---|
elektrolytische Reduktion an Quecksilber-Kathoden; |
Conditions | Yield |
---|---|
elektrolytische Reduktion an Quecksilber-Kathoden; |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 40℃; for 8h; Catalytic behavior; Reagent/catalyst; | 100% |
With palladium; oxygen; sodium hydrogencarbonate In water at 80℃; for 6h; Reagent/catalyst; | 100% |
With titanium(IV) oxide; oxygen at 29.84℃; under 760.051 Torr; for 6h; Sealed tube; Irradiation; | 99% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; | 100% |
toluene-4-sulfonic acid at 20℃; | 100% |
With toluene-4-sulfonic acid | 99% |
4-hydroxymethyl-2-methoxyphenol
butan-1-ol
4-(butoxymethyl)-2-methoxyphenol
Conditions | Yield |
---|---|
With Sn-MCM-41 zeolite at 100℃; for 4h; | 100% |
With titanium cation-exchanged montmorillonite (Ti4+-mont) at 30℃; for 5h; Inert atmosphere; chemoselective reaction; | 98% |
With sulfated tungstate at 80℃; for 3h; Green chemistry; chemoselective reaction; | 83% |
Conditions | Yield |
---|---|
lipase PS-C "Amano" I In toluene at 40℃; for 22h; ceramic; Product distribution / selectivity; | 98% |
Novozym 435 at 50℃; for 20 - 48h; Polyacrylate; Product distribution / selectivity; | 94.1% |
Novozym 435 In hexane at 50℃; for 48h; Polyacrylate; Product distribution / selectivity; | 93.1% |
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 15h; Reflux; | 98% |
ethanol
4-hydroxymethyl-2-methoxyphenol
phenol, 4-(ethoxymethyl)-2-methoxy-
Conditions | Yield |
---|---|
at 80℃; for 2h; Neat (no solvent); | 97% |
Conditions | Yield |
---|---|
at 80℃; for 2h; Neat (no solvent); | 97% |
4-hydroxymethyl-2-methoxyphenol
benzyl bromide
4-benzyloxy-3-methoxybenzyl alcohol
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In toluene Heating; | 96% |
With potassium carbonate In methanol Inert atmosphere; Reflux; | 70.3% |
With 18-crown-6 ether; potassium carbonate for 9h; Reflux; | |
In methanol at 60℃; for 12h; |
Conditions | Yield |
---|---|
96% |
4-hydroxymethyl-2-methoxyphenol
allyl bromide
3-methoxy-4-(2-propenyloxy) benzenemethanol
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 95% |
With potassium carbonate In acetone at 60℃; | 93% |
With potassium carbonate In acetone at 60℃; | 93% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxymethyl-2-methoxyphenol With ammonium formate In ethanol; water at 22℃; for 0.166667h; Stage #2: With formic acid In ethanol; water at 22℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; chemoselective reaction; | 95% |
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene for 3h; Heating; | 87% |
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.166667h; Inert atmosphere; | 96 %Chromat. |
Conditions | Yield |
---|---|
at 80℃; for 2h; Neat (no solvent); | 95% |
With alumina at 180℃; under 11251.1 Torr; for 0.666667h; Microwave irradiation; Sealed tube; | 63% |
Dimethoxymethane
4-hydroxymethyl-2-methoxyphenol
2-methoxy-4-((methoxymethoxy)methyl) phenol
Conditions | Yield |
---|---|
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00833333h; Microwave irradiation; | 95% |
With 1-butyl-3-methylimidazolium tetrachloroindate for 0.0416667h; Microwave irradiation; chemoselective reaction; | 94% |
phosphotungstic acid at 20℃; for 2h; | 93% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone for 48h; Heating; | 94% |
With potassium carbonate; potassium iodide In acetone for 48h; Heating / reflux; | 94% |
Conditions | Yield |
---|---|
With pentafluorophenylboronic acid In toluene for 16h; Friedel-Crafts arylation; Reflux; Molecular sieve; | 94% |
4-hydroxymethyl-2-methoxyphenol
aniline
N-(4-hydroxy-3-methoxybenzylidene)aniline
Conditions | Yield |
---|---|
With CeO2 nanorods anchored on mesoporous carbon; air In toluene at 80℃; under 760.051 Torr; for 2h; | 94% |
With TiO2 supported on MIL-101 framework, modified with CdS nanocrystals and decorated with co-catalytic Ni nanoparticles (Ni/CdS/TiO2-MIL-101) In acetonitrile at 27℃; for 48h; Inert atmosphere; Irradiation; | 72 %Chromat. |
With γ-iron(III) oxide In toluene at 80℃; under 760.051 Torr; for 8h; | 81.2 %Chromat. |
4-hydroxymethyl-2-methoxyphenol
2-phenyl-1-(2-thioxothiazolidin-3-yl)ethan-1-one
2-methoxy-4-hydroxymethylphenyl phenylacetate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 0.05h; Ambient temperature; | 93% |
formaldehyde diethyl acetal
4-hydroxymethyl-2-methoxyphenol
4-((ethoxymethoxy)methyl)-2-methoxy phenol
Conditions | Yield |
---|---|
phosphotungstic acid at 20℃; for 3h; | 93% |
With 1-butyl-3-methylimidazolium tetrachloroindate for 0.0416667h; Microwave irradiation; chemoselective reaction; | 93% |
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00833333h; Microwave irradiation; | 93% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone; toluene Reflux; | 93% |
With tetrabutylammomium bromide; potassium carbonate In acetone Reflux; | |
With potassium carbonate; potassium iodide In acetone at 75℃; for 8h; |
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; boron trifluoride diethyl etherate; iodosylbenzene In dichloromethane at 20℃; for 0.5h; | 92% |
4-hydroxymethyl-2-methoxyphenol
acetyl chloride
4-acetoxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With calcium oxide In 2-methyltetrahydrofuran at 20℃; for 6h; Green chemistry; chemoselective reaction; | 91% |
In tetrahydrofuran at 60℃; for 0.5h; Microwave irradiation; | 100 %Spectr. |
IUPAC Name: 4-(Hydroxymethyl)-2-methoxyphenol
Empirical Formula: C8H10O3
Molecular Weight: 154.1632g/mol
EINECS: 207-852-4
Structure of 4-Hydroxy-3-methoxybenzyl alcohol (CAS NO.498-00-0):
Index of Refraction: 1.57
Molar Refractivity: 41.26 cm3
Molar Volume: 125.6 cm3
Polarizability: 16.35×10-24cm3
Surface Tension: 48.9 dyne/cm
Density: 1.226 g/cm3
Flash Point: 143.2 °C
Enthalpy of Vaporization: 58.51 kJ/mol
Melting Point: 110-117 °C(lit.)
Boiling Point: 313.1 °C at 760 mmHg
Vapour Pressure: 0.000216 mmHg at 25 °C
Stability: Stable. Incompatible with strong oxidizing agents, strong acids.
Product Categories: Benzhydrols, Benzyl & Special Alcohols
Canonical SMILES: COC1=C(C=CC(=C1)CO)O
InChI: InChI=1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3
InChIKey: ZENOXNGFMSCLLL-UHFFFAOYSA-N
Safety Information of 4-Hydroxy-3-methoxybenzyl alcohol (CAS NO.498-00-0):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant
4-Hydroxy-3-methoxybenzyl alcohol , its cas register number is 498-00-0. It also can be called 4-Hydroxy-3-methoxybenzenemethanol ; 4-Hydroxy-3-methoxybenzyl alcohol ; 4-Hydroxy-3-methoxyphenylmethanol ; AI3-24186 ; Benzenemethanol, 4-hydroxy-3-methoxy- ; Vanillic alcohol ; Vanillin alcohol ; Vanillyl alcohol . 4-Hydroxy-3-methoxybenzyl alcohol (CAS NO.498-00-0) is crystalline white to off-white powder .
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