1-(2-Benzyloxyphenyl)-4-(2-chlorophenyl)butane → 2-[4-(2-Chlorophenyl)butyl]phenol

HRID 743405Notes

Reaction equation

HRID 743405 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])C1C=CC=CC=1>C(Cl)Cl.B(Br)(Br)Br>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][CH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 194240181-(2-Benzyloxyphenyl)-4-(2-chlorophenyl)butane

Product 1

HCID 194239572-[4-(2-Chlorophenyl)butyl]phenolYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

Finally, following a procedure similar to that described in the final part of Preparation 15, the whole of this 1-(2-benzyloxyphenyl)-4-(2-chlorophenyl)butane was dissolved in 18 ml of methylene chloride and debenzylated by means of 8.15 ml of a 1M solution of boron tribromide in methylene chloride. The crude product thus obtained was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.0 g (yield 94%) of the title compound as a colorless solid.

Workup

  1. custompart of Preparation 15
  2. customThe crude product thus obtained
  3. customwas purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-02e7ef9f537a4ad8b9f2fd571bb3557f
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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