Sodium borohydride → HCID 21554200, compound

HRID 267808Notes

Reaction equation

HRID 267808 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH2:3]1.[BH4-].[Na+]>CO.O>[OH:16][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH:4]=2)=[CH:9][CH:10]=1)[CH3:15]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21554184HCID 21554184, compound

Product 1

HCID 21554200HCID 21554200, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

8.8 g of para-(4-methyl-1-cyclohexenyl)-acetophenone are stirred portionwise into a solution, cooled to 0°C, of 1.8 g of sodium borohydride in 80 ml of methanol and 15 ml of water. Stirring is continued at 5°-10°C for an hour and a half and at room temperature for 4 hours, 200 ml of water are added, and the batch then extracted with 3 × 100 ml of methylene chloride. The methylene chloride residue is recrystallized from petroleum ether and yields 1-hydroxy-1-[para-(4-methyl-1-cyclohexenyl)-phenyl]-ethane of melting point 65°-67°C.

Workup

  1. waitis continued at 5°-10°C for an hour
  2. extractionthe batch then extracted with 3 × 100 ml of methylene chloride
  3. customThe methylene chloride residue is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-b2b725eb33d44714ac58dd4520350a6a
Source dataset
uspto-grants-1976_03
Patent number
US03944589

Reaction notes

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