Water → Diphenylmethane

HRID 649233Notes

Reaction equation

HRID 649233 reaction equation
C([Li])CCC.C(C1N=CN([C:16](C2C=CC=CC=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)C=1)(=O)CCC.[Cl-].[NH4+].O>C1COCC1.CCCCCC>[C:17]1([CH2:16][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 147363744-Butanoyl-1-trityl-imidazoleHCID 178418339Butyllithium

Product 1

HCID 7580DiphenylmethaneYield 200%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 4.30 g (25.8 mmols) of diphenylmethane in 50 ml of THF is prepared in inert atmosphere (nitrogen) then cooled in an ice bath. First 16.7 ml of butyllithium of a 1.7M solution in hexane and then, drop by drop, a solution of 4.90 g (12.9 mmols) of the previous ketone 3 in 50 ml of THF, are added slowly. The resultant mixture is stirred for 2 hours at room temperature and then 50 ml of a saturated aqueous solution of ammonium chloride and 100 ml of water are added. Extraction with ethyl acetate followed by evaporation of the previously dried extracts yields alcohol 4 which is recrystallised in cyclohexane.

Workup

  1. temperaturethen cooled in an ice bath
  2. extractionExtraction with ethyl acetate
  3. customfollowed by evaporation of the previously dried extracts

Sources & evidence

ORD record
ord-706d9badff444c799cbd39809ca4d99a
Source dataset
uspto-grants-1988_04
Patent number
US04738979

Reaction notes

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