Acetic Acid → Ethyl 4-methoxy-α-methyl-γ-oxobenzenebutanoate

HRID 221829Notes

Reaction equation

HRID 221829 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.Br.[CH3:18][C:19](O)=O>>[CH2:18]([O:13][C:12](=[O:14])[CH:11]([CH3:15])[CH2:10][C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[O:16])[CH3:19]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 125148794-(4-Methoxyphenyl)-2-methyl-4-oxobutanoic acid

Product 1

HCID 67009765Ethyl 4-methoxy-α-methyl-γ-oxobenzenebutanoateYield 93%

Procedure

A solution of 4-(4-methoxyphenyl)-2-methyl-4-oxobutyric acid (10 g, 45 mmol) and 150 mL of 48% HBr in 20 mL of AcOH was heated to 100° C. for 48 h. The solvent was evaporated and EtOH (3×30 mL) was added and evaporated to give 4-(4-methoxy-phenyl)-2-methyl-4-oxobutyric acid ethyl ester (9.96 g, 93%); MS m/z 259 (M+23).

Workup

  1. customThe solvent was evaporated
  2. additionEtOH (3×30 mL) was added
  3. customevaporated

Sources & evidence

ORD record
ord-e706b2647ef34d09a8609eb0783901fd
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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