Water → (S)-(+)-4'-(2-Methylbutyl)-[1,1'-biphenyl]-4-ol

HRID 2072634Notes

Reaction equation

HRID 2072634 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:23])[CH2:21][CH3:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.O>C(Cl)Cl>[CH3:23][CH:20]([CH2:21][CH3:22])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 117369194'-Methoxy-4-(2-methylbutyl)biphenyl

Product 1

HCID 11195818(S)-(+)-4'-(2-Methylbutyl)-[1,1'-biphenyl]-4-olYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 33 m moles (8.2 g) of boron tribromide in 25 ml of methylene chloride was cooled to -70° C., and a solution of 28 m moles (7.0 g) of 4'-methoxy-4-(2-methylbutyl)biphenyl in 150 ml of methylene chloride was added dropwise thereto. The mixture was returned to room temperature in 8 hours, and then stirred for five hours. After addition of water, the reaction mixture was extracted with methylene chloride, then purified by column chromatography to obtain 4.0 g of 4'-(2-methylbutyl)-4-hydroxybiphenyl. (yield: 60%)

Workup

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-16e1f0d362864aa9b3ed63d9f2b76b18
Source dataset
uspto-grants-1990_04
Patent number
US04913839

Reaction notes

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