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

HRID 984303

Reaction equation

HRID 984303 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-27295cf882084791ba5c76008a40c68f
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Linked notes

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