Water → (4-Hydroxyphenyl)(3-methylphenyl)methanone

HRID 228601

Reaction equation

HRID 228601 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br.ClCCl.O>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12469466(4-Methoxyphenyl)(3-methylphenyl)methanoneHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 22132621(4-Hydroxyphenyl)(3-methylphenyl)methanoneYield 265.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Methoxyphenyl)(3-methylphenyl)methanone (603 mg) was dissolved in dichloromethane (3 ml) to prepare a solution. A boron tribromide-dichloromethane solution (1.0 M) (11 ml) was added to the solution, and the mixture was stirred at room temperature for 2 days. The reaction solution was poured into ice-cooled water, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was subjected to separation and purification by column chromatography on silica gel using hexane/ethyl acetate as a solvent to give (4-hydroxyphenyl)(3-methylphenyl)methanone (1.50 g, yield 56%).

Workup

  1. customto prepare a solution
  2. additionThe reaction solution was poured into ice-
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialwas dried over sodium sulfate
  6. concentrationwas then concentrated
  7. customThe residue was subjected to separation and purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-32e8ef05d2084566b2a7db68dcf6d5f0
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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