Methyl 4-(1-hydroxy-3-methylbutyl)benzoate → Methyl 4-(3-methylbutanoyl)benzoate

HRID 658304Notes

Reaction equation

HRID 658304 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 59518172Methyl 4-(1-hydroxy-3-methylbutyl)benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 56593012Methyl 4-(3-methylbutanoyl)benzoateYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(1-hydroxy-3-methyl-butyl)-benzoic acid methyl ester (19.72 g, 88.78 mmol) in dichloromethane (300 mL) is added pyridinium chlorochromate (22.03 g, 97.65 mmol). The mixture is allowed to stir at room temperature, and the solution turns black over time. The reaction is monitored by HPLC. Upon complete conversion, the reaction is diluted with dichloromethane and silica gel (2% by weight) is added to the mixture. The mixture is purified by flash column chromatography using dichloromethane as mobile phase, producing 15.79 g (72%) of product. MS (ES): 221.3 (M+1)+.

Workup

  1. additionis added to the mixture
  2. customThe mixture is purified by flash column chromatography

Sources & evidence

ORD record
ord-33ece0c7f52e45a3a0b553eddd087da7
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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