Sodium borohydride → HCID 21554236, compound

HRID 267807Notes

Reaction equation

HRID 267807 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[BH4-].[Na+]>CO.O>[OH:16][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)=[CH:9][CH:10]=1)[CH3:15]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21484453HCID 21484453, compound

Product 1

HCID 21554236HCID 21554236, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 49 g of this ketone in 100 ml of methanol is stirred dropwise into a solution, cooled to 0° C, of 11 g of sodium borohydride in 500 ml of methanol and 100 ml of water. The reaction solution is stirred for another hour and a half at 5° to 10° C and then allowed to stand at room temperature for 16 hours. Finally, 600 ml of water are added and the batch is extracted with methylene chloride, dried over sodium sulfate and evaporated. In this manner, 1-hydroxy-1-[para-(1-cycloheptenyl)-phenyl]-ethane is obtained as an oily, colorless residue.

Workup

  1. customat 5° to 10° C
  2. extractionthe batch is extracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-a78fd18ea67f42249f77a618e1fdf578
Source dataset
uspto-grants-1976_03
Patent number
US03944589

Reaction notes

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