<3-(allyloxy)phenyl>acetic acid
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1h; | 98% |
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 12h; | 85% |
Conditions | Yield |
---|---|
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 100℃; for 6h; | 71% |
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h; | 71% |
Conditions | Yield |
---|---|
With caesium carbonate In methanol for 1h; UV-irradiation; Inert atmosphere; | A 53% B 45% |
methanol
3-chlorophenylacetic acid
A
benzyl methyl ether
B
3-hydroxyphenylacetic acid
C
benzyl alcohol
Conditions | Yield |
---|---|
With caesium carbonate In aq. buffer for 1h; UV-irradiation; Inert atmosphere; | A 8% B 47% C 34% |
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With indium; deuterated ammonium chloride In tetrahydrofuran-d8; water-d2 at 20℃; for 24h; Reflux; chemoselective reaction; | 32% |
Conditions | Yield |
---|---|
With sodium hydroxide; aluminum nickel |
Conditions | Yield |
---|---|
With diammonium sulfide; sulfur; isopropyl alcohol at 160℃; Erhitzen des von Ammoniak, Schwefelwasserstoff und Isopropylalkohol befreiten Reaktionsgemisches mit wss. Natronlauge; | |
Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogen iodide | |
With hydrogen iodide |
3-Hydroxyphenylacetonitrile
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
3-amino phenylacetic acid
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With sodium nitrite |
α,3-dihydroxybenzeneacetonitrile
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With phosphorus; hydrogen iodide |
phenylacetic acid
A
4-hydroxyphenylacetate
B
3-hydroxyphenylacetic acid
C
2-Hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With iron(III) sulfate; dihydrogen peroxide; 3,4-dioxo-3,4-dihydronaphthalene-1-sulfonate In water Yield given. Yields of byproduct given; | |
With Fe2(SO4); dihydrogen peroxide; 3,4-dioxo-3,4-dihydronaphthalene-1-sulfonate In water Product distribution; | |
With dihydrogen peroxide; iron(III); benzene-1,2-diol In water Product distribution; Ambient temperature; further redox-systems and aromatic compounds investigated; |
phenylacetic acid
A
4-hydroxyphenylacetate
B
3-hydroxyphenylacetic acid
C
homogentisic acid
D
2-(2,6-dihydroxyphenyl)acetic acid
E
2-Hydroxyphenylacetic acid
Conditions | Yield |
---|---|
In various solvent(s) at 30℃; for 170h; Product distribution; Mechanism; biosynthesis by Trichosporum cutaneum strains, pH = 6, other incubation times; |
Conditions | Yield |
---|---|
With n-butyllithium; potassium tert-butylate 1.) hexane, reflux, 3 h, 2.) THF; Yield given. Multistep reaction; |
3-hydroxy-4-isopropylphenylacetic acid
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
(i) CH2N2, Et2O, (ii) AlCl3, PhCl; Multistep reaction; |
Conditions | Yield |
---|---|
man behandelt mit KCN und kocht das entstandene rohe 3-Methoxy-mandelsaeurenitril mit Jodwasserstoffsaeure; |
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
at 160℃; und Erhitzen des von NH3, H2S und Isopropylalkohol befreiten Reaktionsgemisches mit wss.NaOH auf Siedetemperatur; |
Conditions | Yield |
---|---|
man kocht das Reaktionsprodukt mit Jodwasserstoffsaeure; |
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 200℃; im geschlossenen Rohr; |
Conditions | Yield |
---|---|
at 200℃; im geschlossenen Rohr; |
2-(3-hydroxyphenyl)ethanol
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
With Serratia marcescens In water at 30℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tin; hydrochloric acid 2: diluted hydrochloric acid; NaNO2 3: concentrated hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diluted hydrochloric acid; NaNO2 2: concentrated hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: bei der Nitrierung 2: tin; hydrochloric acid 3: diluted hydrochloric acid; NaNO2 4: concentrated hydrochloric acid View Scheme |
6-isopropyl 6-acetoxy cyclohexa-2,4-dienone
3-hydroxyphenylacetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i), (ii) (alkaline hydrolysis) 2: (i) CH2N2, Et2O, (ii) AlCl3, PhCl View Scheme |
phenylacetic acid
A
3-hydroxyphenylacetic acid
B
3,4-dihydroxyphenylacetate
C
homogentisic acid
Conditions | Yield |
---|---|
With sulfuric acid; water at 30℃; for 34h; Electrolysis; |
3-hydroxyphenylacetic acid
2-(3-hydroxyphenyl)ethanol
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 0℃; for 1h; | 100% |
Stage #1: m-hydroxyphenylacetic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; for 2h; Stage #2: With hydrogenchloride; water In tetrahydrofuran | 88% |
Stage #1: m-hydroxyphenylacetic acid With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 3h; Heating / reflux; Stage #2: With water In tetrahydrofuran | 85% |
Conditions | Yield |
---|---|
thionyl chloride at 20℃; for 6h; | 100% |
thionyl chloride at 20℃; for 6h; | 100% |
With sulfuric acid Reflux; | 100% |
3-hydroxyphenylacetic acid
recorcinol
1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)ethanone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate for 1.5h; Reflux; | 100% |
With boron trifluoride diethyl etherate at 60 - 70℃; for 1h; | 93% |
With boron trifluoride diethyl etherate In toluene at 90℃; for 2h; | 57% |
With boron trifluoride diethyl etherate at 110℃; for 2h; Inert atmosphere; | |
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 90℃; for 2h; |
methanol
3-hydroxyphenylacetic acid
3-hydroxy-benzeneacetic acid, methyl ester
Conditions | Yield |
---|---|
With sulfuric acid for 8h; Heating; | 100% |
With sulfuric acid for 18h; Heating / reflux; | 100% |
With sulfuric acid for 18h; Heating / reflux; | 100% |
3-hydroxyphenylacetic acid
trimethyl orthoformate
3-hydroxy-benzeneacetic acid, methyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 4h; Heating; | 100% |
With toluene-4-sulfonic acid In methanol for 5h; Reflux; | |
With toluene-4-sulfonic acid In methanol for 5h; Reflux; |
3-hydroxyphenylacetic acid
3-hydroxy-benzeneacetic acid, methyl ester
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 18h; Heating / reflux; | 100% |
With thionyl chloride In methanol; hexane; ethyl acetate | 94% |
27.8 g (100%) | |
With sodium bicarbonate In methanol |
3-hydroxyphenylacetic acid
3-hydroxy-benzeneacetic acid, methyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol | 100% |
3-hydroxyphenylacetic acid
N,O-dimethylhydroxylamine*hydrochloride
2-(3-hydroxyphenyl)-N-methoxy-N-methylacetamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere; | 100% |
3-hydroxyphenylacetic acid
2-(3-hydroxycyclohexyl)acetic acid
Conditions | Yield |
---|---|
With hydrogen; Rh on carbon In sodium hydroxide at 60℃; under 760 Torr; for 3h; | 99% |
With rhodium contaminated with carbon; hydrogen; sodium hydroxide In water at 80℃; under 7500.75 Torr; for 12h; | 600 mg |
3-hydroxyphenylacetic acid
benzyl bromide
phenylmethyl 2-[3-(phenylmethoxy)phenyl]acetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 99% |
With potassium carbonate In N,N-dimethyl-formamide | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h; | 92% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 72h; Etherification; | 83% |
With potassium carbonate In N-methyl-acetamide |
3-hydroxyphenylacetic acid
diazomethyl-trimethyl-silane
3-hydroxy-benzeneacetic acid, methyl ester
Conditions | Yield |
---|---|
In methanol; hexane; toluene | 99% |
3-hydroxyphenylacetic acid
allyl bromide
<3-(allyloxy)phenyl>acetic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 15h; Heating; | 98% |
With n-Bu4POH In tetrahydrofuran; water at 0 - 20℃; | 83% |
Stage #1: m-hydroxyphenylacetic acid; allyl bromide With potassium carbonate In ethanol for 5h; Reflux; Stage #2: With potassium hydroxide In ethanol at 20℃; for 12h; | 71.2% |
Stage #1: m-hydroxyphenylacetic acid; allyl bromide With potassium carbonate In ethanol at 70℃; for 5h; Stage #2: With potassium hydroxide In ethanol at 20℃; for 12h; | 71.2% |
Conditions | Yield |
---|---|
In ethanol; water | 97% |
11.66 g (98%) |
3-hydroxyphenylacetic acid
L-alanine benzyl ester hydrochloride
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 95% |
3-hydroxyphenylacetic acid
2-bromomethylnaphthyl bromide
3-(naphth-2-ylmethoxy)phenylacetic acid
Conditions | Yield |
---|---|
With sodium hydroxide; concentrated aqueous hydrochloric acid; potassium carbonate In ethanol; acetone | 94% |
Conditions | Yield |
---|---|
With sulfuric acid-d2 at 60℃; for 1h; Sealed tube; | 94% |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium iodide In ethanol for 16h; Heating; | 93% |
With potassium iodide; potassium hydroxide In tetrahydrofuran for 18h; Reflux; | 91% |
Stage #1: m-hydroxyphenylacetic acid With thionyl chloride In methanol at 0℃; for 4h; Heating / reflux; Stage #2: benzyl bromide With potassium carbonate In acetone at 20℃; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages; | 91% |
3-hydroxyphenylacetic acid
3-acetoxyphenylacetic acid
Conditions | Yield |
---|---|
With pyridine In P2O5; water; acetic anhydride | 90% |
With pyridine In P2O5; water; acetic anhydride |
3-hydroxyphenylacetic acid
2-(3,4-dimethoxyphenyl)-ethylamine
N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-(3-hydroxy-phenyl)-acetamide
Conditions | Yield |
---|---|
89% | |
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; |
3-hydroxyphenylacetic acid
(3S)-3-(4-fluoro-3-nitrophenyl)-2-<(2R)-2-(4-hydroxy-phenyl)-2-<2-(3-hydroxyphenyl)-acetylamino>acetylamino>-propionic acid methyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane | 89% |
3-hydroxyphenylacetic acid
4-fluoroaniline
N-(4-fluorophenyl)-2-(3-hydroxyphenyl)acetamide
Conditions | Yield |
---|---|
89% |
3-hydroxyphenylacetic acid
4-{[2-(chloromethyl)phenoxy]methyl}-5-methyl-2-phenyl-1,3-oxazole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 1 - 30℃; | 89% |
3-hydroxyphenylacetic acid
benzyl bromide
benzyl (3-hydroxyphenyl)acetate
Conditions | Yield |
---|---|
Stage #1: m-hydroxyphenylacetic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 48h; | 89% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 70℃; | 87% |
3-hydroxyphenylacetic acid
1,1,1,3,3,3-hexamethyl-disilazane
2-[3-(trimethylsilyloxy)phenyl]acetic acid
Conditions | Yield |
---|---|
With cross-linked poly((30percent)4-vinylpyridine/(70percent)styrene) copolymer-supported bismuth(III) triflate In dichloromethane at 20℃; for 0.333333h; | 88% |
Conditions | Yield |
---|---|
With triethylamine at 100 - 170℃; Microwave irradiation; | 87% |
3-hydroxyphenylacetic acid
phenethylamine
2-(3-hydroxyphenyl)-N-phenethylacetamide
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 85% |
2-hydroxy-5-methylbenzaldehyde
3-hydroxyphenylacetic acid
acetic anhydride
Conditions | Yield |
---|---|
With triethylamine at 120℃; for 8h; | 85% |
Conditions | Yield |
---|---|
With triethylamine at 100 - 170℃; Microwave irradiation; | 85% |
1. Introduction of 3-Hydroxyphenylacetic acid
3-Hydroxyphenylacetic acid, with the CAS registry number 621-37-4, is also known as 3-Hydroxyphenylacetic acid. It belongs to the product categories of Aromatic Phenylacetic Acids and Derivatives; Aromatics; Carbonyl Compounds; Carboxylic Acids. What's more, its IUPAC name is 2-(3-hydroxyphenyl)acetic acid.
2. Properties of 3-Hydroxyphenylacetic acid
(1)ACD/LogP: 0.77; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.58; (4)ACD/LogD (pH 7.4): -2.35; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.78; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 35.53 Å2; (13)Index of Refraction: 1.596; (14)Molar Refractivity: 39.24 cm3; (15)Molar Volume: 115.3 cm3; (16)Surface Tension: 59.8 dyne/cm; (17)Density: 1.319 g/cm3; (18)Flash Point: 179.1 °C; (19)Enthalpy of Vaporization: 62.63 kJ/mol; (20)Boiling Point: 349 °C at 760 mmHg; (21)Vapour Pressure: 1.81E-05 mmHg at 25°C.
3. Structure Descriptors of 3-Hydroxyphenylacetic acid
(1)Canonical SMILES: C1=CC(=CC(=C1)O)CC(=O)O
(2)InChI: InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
(3)InChIKey: FVMDYYGIDFPZAX-UHFFFAOYSA-N
4. Safety Information of 3-Hydroxyphenylacetic acid
Hazard Symbols:Xi
Risk Codes:
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Description:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
5. Preparation of 3-Hydroxyphenylacetic acid
3-Hydroxyphenylacetic acid can be prepared by (3-hydroxy-phenyl)-acetic acid and 3-bromo-propene by heating. This reaction will need reagent NaH and solvent tetrahydrofuran. The reaction time is 15 hours. The yield is about 98%.
6. Use of 3-Hydroxyphenylacetic acid
3-Hydroxyphenylacetic acid can be used to produce ethyl 3-hydroxyphenylacetate by heating. It will need reagent H2SO4 with reaction time of 7 hours. The yield is about 94%.
7. Other details of 3-Hydroxyphenylacetic acid
When you are using this chemical, please be cautious about it as the following:
3-Hydroxyphenylacetic acid is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You need wear suitable protective clothing.
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