Water → Methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoate

HRID 228718Notes

Reaction equation

HRID 228718 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23078435Methyl 8-(2-methoxy-5-methylphenyl)-8-oxo-octanoate

Product 1

HCID 23078392Methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoateYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 8-(2-methoxy-5-methyl-phenyl)-8-oxo-octanoate (992 mg) was dissolved in methylene chloride (30 ml) to prepare a solution. 1 M boron tribromide (5.0 ml) was added at −78° C. to the solution, and the mixture was stirred at room temperature for 30 min. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoate (271 mg, yield 29%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d989e60f24574ba9a8b000e932ecdf71
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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