[2-(5-Phenylpentyloxy)phenyl]methanol → Triphenyl[2-(5-phenylpentyloxy)benzyl]phosphonium bromide

HRID 1672629

Reaction equation

HRID 1672629 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:21].[C:22]1([PH+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[Br-:21].[C:35]1([P+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 20764199[2-(5-Phenylpentyloxy)phenyl]methanolHCID 22178555Triphenylphosphonium hydrobromide

Product 1

HCID 22560990Triphenyl[2-(5-phenylpentyloxy)benzyl]phosphonium bromideYield 93.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 18.7 g (69.16 mmol) of [2-(5-phenylpentyloxy)phenyl]methanol from Example 27A in 120 ml of acetonitrile is mixed with 22.55 g (65.71 mmol) of triphenylphosphonium hydrobromide and heated to reflux for three hours. The reaction solution is then concentrated to dryness. 36.6 g (61.45 mmol, 83% yield) of crystalline product are obtained and are reacted without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. concentrationThe reaction solution is then concentrated to dryness

Sources & evidence

ORD record
ord-048e4ae8aa1e4349bdcd5635f748593f
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Linked notes

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