(E)-2-chloro-4-[3-(3-hydroxyphenyl)-1-oxoprop-2-en-1-yl]benzoic acid methyl ester → 2-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester

HRID 1058393Notes

Reaction equation

HRID 1058393 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:20])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[CH:6][C:5]=1[Cl:21]>C(OCC)(=O)C.[Pd]>[Cl:21][C:5]1[CH:6]=[C:7]([C:10](=[O:20])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:22].[Cl:21][C:5]1[CH:6]=[C:7]([CH:10]([OH:20])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:22]

Participants

5

Reactant 1

HCID 23560779(E)-2-chloro-4-[3-(3-hydroxyphenyl)-1-oxoprop-2-en-1-yl]benzoic acid methyl ester

Product 2

HCID 235607782-Chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl esterYield 26%HCID 235607802-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl esterYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture (E)-2-chloro-4-[3-(3-hydroxyphenyl)-1-oxoprop-2-en-1-yl]benzoic acid methyl ester (Example 91; 250 mg, 0.8 mmol) and 10% palladium-on-charcoal (25 mg) in ethyl acetate (5 mL) was hydrogenated at atmospheric pressure for 90 min. The reaction mixture was filtered through Celite® and the filter cake was washed with ethyl acetate. The solvent was evaporated under reduced pressure and the residue was then chromatographed over silica gel (20-50% ethyl acetate/hexanes) to give 2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoic acid, methyl ester (160 mg, 64% yield) and rac.-2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoic acid, methyl ester (65 mg, 26% yield). The alcohol was obtained as a racemic mixture and was not resolved.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washthe filter cake was washed with ethyl acetate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was then chromatographed over silica gel (20-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3febfeed252543ef902356fd5d00b4af
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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