Toluene → (E)-3-biphenyl-4-yl-but-2-en-1-ol

HRID 1268248

Reaction equation

HRID 1268248 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)[CH:21]=[C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[CH3:23])C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CO>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24](/[C:22](/[CH3:23])=[CH:21]/[CH2:20][OH:19])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 545016723-(4-Biphenylyl)-2-butenoic acid ethyl ester

Product 1

HCID 11264581(E)-3-biphenyl-4-yl-but-2-en-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of DIBAL-H in toluene (40 ml, 40 mmol) was added dropwise at −70° C. over 20 min. to a stirred solution of 3-biphenyl-4-yl-but-2-enoic acid ethyl ester (2.66 g, 10.0 mmol) in dry THF (100 ml) and the mixture stirred for 30 min. Methanol (2 ml) was added, followed by saturated aqueous Rochelle's salt (100 ml), and the resulting mixture extracted with ethyl acetate (200 ml), separated and the organic phase washed with brine, dried (Na2SO4), evaporated and dried in vacuo yielding (E)-3-biphenyl-4-yl-but-2-en-1-ol as colorless crystals: 1.94 g (86%)

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate (200 ml)
  2. customseparated
  3. washthe organic phase washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-70ad7948834c4cd2b142573fa6258aa4
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Linked notes

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