Water → 1-[4'-(Hydroxymethyl)-phenyl]-3-phenyl-trans-1-butene

HRID 845871Notes

Reaction equation

HRID 845871 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])=[CH:6][CH:5]=1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:2][CH2:1][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[CH:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 141829521-(4'-Carboxyphenyl)-3-phenyl-trans-1-buteneHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 201305691-[4'-(Hydroxymethyl)-phenyl]-3-phenyl-trans-1-butene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(4'-carboxyphenyl)-3-phenyl-trans-1-butene (0.35 g, 1.5 mmol) in tetrahydrofuran (25 ml) was added dropwise to a suspension of lithium aluminum hydride (56 mg) in tetrahydrofuran. The reaction was refluxed for 3 hours and cooled to ambient temperature. Excess lithium aluminum hydride was decomposed by the sequential addition of water (0.1 ml), 15% aqueous sodium hydroxide (0.1 ml) and water (0.3 ml). The precipitate was removed by filtration and the filtrate evaporated. The residue was subjected to column chromatography on silica gel (E. Merck No. 7734). Elution with 3:1 hexane-ether afforded pure 1-[4'-(hydroxymethyl)-phenyl]-3-phenyl-trans-1-butene; yield 0.22 g (65%); mass spectrum m/z: 238 (M), 223 (M--CH3).

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. customThe precipitate was removed by filtration
  3. customthe filtrate evaporated
  4. washElution with 3:1 hexane-ether afforded pure 1-[4'-(hydroxymethyl)-phenyl]-3-phenyl-trans-1-butene

Sources & evidence

ORD record
ord-c794be5577b34647b083cec50c40fd79
Source dataset
uspto-grants-1988_07
Patent number
US04760161

Reaction notes

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