Acetic Acid → 1-(2,5-Dimethoxyphenyl)-2-methyl-4-phenyl-1-butene

HRID 1706261Notes

Reaction equation

HRID 1706261 reaction equation
C([Li])CCC.[Br-].[CH3:7][O:8][C:9]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:10]=1[CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:37]([CH2:44][C:45](=O)[CH3:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(O)(=O)C>O1CCCC1>[CH3:7][O:8][C:9]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:10]=1[CH:11]=[C:45]([CH3:46])[CH2:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 17355Benzyl acetoneHCID 19605777(2,5-Dimethoxybenzyl)(triphenyl)phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 538935181-(2,5-Dimethoxyphenyl)-2-methyl-4-phenyl-1-butene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyl lithium (29 ml. of 2.2 M) is added dropwise to 2,5-dimethoxybenzyl triphenylphosphonium bromide (31.5 g.) in tetrahydrofuran (200 ml.) with stirring and the resulting deep red solution is stirred for one-half hour. Benzyl acetone (9.4 g.) is added dropwise and the reaction mixture stirred for 12 hours. It is then adjusted to pH 7 by addition of acetic acid and concentrated under reduced pressure. The residue is extracted with methylene chloride and the extract evaporated to give crude 1-(2,5-dimethoxyphenyl)-2-methyl-4-phenyl-1-butene as an oil. It is purified by chromatography on silica gel and elution with benzene.

Workup

  1. stirringthe resulting deep red solution is stirred for one-half hour
  2. stirringthe reaction mixture stirred for 12 hours
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue is extracted with methylene chloride
  5. customthe extract evaporated

Sources & evidence

ORD record
ord-14ce2b34e5d0457f9fb24ff54c68fd53
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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