4-METHOXY-3-HYDROXYACETOPHENONE Chemical Properties

Melting point:

88-92 °C

Boiling point:

329.9±27.0 °C(Predicted)

Density 

1.158

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.15±0.10(Predicted)

color 

Off-White to Yellow

Stability:

Stable. Incompatible with strong oxidizing agents.

InChI

InChI=1S/C9H10O3/c1-6(10)7-3-4-9(12-2)8(11)5-7/h3-5,11H,1-2H3

InChIKey

YLTGFGDODHXMFB-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(OC)C(O)=C1)C

LogP

1.373 (est)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2914390090

4-METHOXY-3-HYDROXYACETOPHENONE Usage And Synthesis

Chemical Properties

solid

Uses

Isoacetovanillone (Diosmin EP Impurity A) is a volatile compound isolated from oak wood. Also a byproduct in the production of Acetovanillone.

Uses

Isoacetovanillone is a volatile compound isolated from oak wood. Also a byproduct in the production of Acetovanillone.

Definition

ChEBI: Isoacetovanillone is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.

Preparation

Preparation by saponification of 3-acetoxy-4-methoxy-acetophenone (90%) (59%).

Synthesis Reference(s)

Synthetic Communications, 18, p. 1379, 1988 DOI: 10.1080/00397918808078806

Synthesis

General procedure for the synthesis of 4-methoxy-3-hydroxyacetophenone from 3'-hydroxy-4'-methoxyacetophenone (12): ketone 8 (250 mg, 1.20 mmol) was dissolved in anhydrous CH2Cl2 (3 mL), AlCl3 (208 mg, 1.56 mmol) was added, and the reaction was stirred for 24 h at 18 °C and under nitrogen protection. After completion of the reaction, the mixture was partitioned between water (10 mL) and CH2Cl2 (10 mL). The aqueous phase was extracted once with CH2Cl2 (10 mL), the organic phases were combined, dried with MgSO4, filtered and concentrated under reduced pressure. The light yellow oil obtained was purified by fast chromatography (eluent: ethyl acetate/hexane, 1:4 v/v) to give a white solid 4-methoxy-3-hydroxyacetophenone 124 (172 mg, 86% yield) with a melting point of 88.6-90.5 °C (literature value: 92-93 °C) and a TLC (silica gel plate, unfolding agent: ethyl acetate/hexane, 1:1 v/v) Rf value was 0.4. 1H NMR (300MHz, CDCl3) δ: 7.53-7.56 (m, 2H), 6.89 (d, J=7.5Hz, 1H), 5.73 (br s, 1H), 3.96 (s, 3H), 2.54 (s, 3H).

References

[1] Patent: WO2008/124878, 2008, A1. Location in patent: Page/Page column 38

4-METHOXY-3-HYDROXYACETOPHENONE(6100-74-9)Related Product Information

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• 3,7,3',4'-TETRAMETHYLGOSSYPETIN
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• EUPATORIN-5-METHYL ETHER
• 2',3',4'-TRIMETHOXYACETOPHENONE
• 3',4',5'-TRIMETHOXYACETOPHENONE
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• 4',6,7-Trimethoxyisoflavone
• 6-Acetyl-1,4-benzodioxane
• 4'-METHOXY-2'-HYDROXYACETOPHENONE,4-METHOXY-2-HYDROXYACETOPHENONE,Methoxy-2-hydroxyAcetophenone
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