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

HRID 642805Notes

Reaction equation

HRID 642805 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 wt) 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-fa98826aa14b4d29b84676cc7aee53d7
Source dataset
uspto-grants-2010_04
Patent number
US07696248B2

Reaction notes

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