Sodium borohydride → HCID 21554190, compound

HRID 267809Notes

Reaction equation

HRID 267809 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1>CO.O>[OH:17][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([C:3]2[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=2)=[CH:10][CH:11]=1)[CH3:16]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 215333951-([2',3',4',5'-Tetrahydro[1,1'-biphenyl]]-4-yl)ethan-1-one

Product 1

HCID 21554190HCID 21554190, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 7 g of sodium borohydride in 300 ml of methanol and 80 ml of water is cooled to 5°C and 50 g of p-(1-cyclohexenyl)-acetophenone are stirred in portionwise. The batch is stirred on for 2 hours at room temperature, the solution is concentrated to half its volume in a rotary evaporator, mixed with 1 litre of water and extracted with 3 × 500 ml of methylenechloride. The methylenechloride residue is recrystallized from petroleum ether and furnishes 1-hydroxy-1-[p-(1-cyclohexenyl)-phenyl]-ethane melting at 60°-62°C.

Workup

  1. concentrationthe solution is concentrated to half its volume in a rotary evaporator
  2. additionmixed with 1 litre of water
  3. extractionextracted with 3 × 500 ml of methylenechloride
  4. customThe methylenechloride residue is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-edddeffe78554bc3a661b6ad1afebe52
Source dataset
uspto-grants-1976_03
Patent number
US03944589

Reaction notes

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