Water → HCID 67937970, compound

HRID 345450Notes

Reaction equation

HRID 345450 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([CH3:18])([CH3:17])[CH2:5]/[C:6](=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)/[CH:7]=[O:8].O>[OH-].[Na+]>[Cl:16][C:13]1[CH:12]=[CH:11][C:10](/[CH:9]=[C:6](\[CH2:7][OH:8])/[CH2:5][C:4]([CH3:3])([CH3:17])[CH3:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 14478616HCID 14478616, compound

Product 1

HCID 67937970HCID 67937970, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2.1 g of sodium borohydride, dissolved in a little 10% strength sodium hydroxide solution, are added to a solution of 47.3 g of Z-2-(2,2-dimethylpropyl)-3-(4-chlorophenyl)-propenal. After the reaction mixture has been stirred for 18 hours at room temperature, 200 ml of water are added to the solution and the resulting emulsion is extracted by shaking with methylene chloride. The organic phase isolated is then dried over sodium sulfate and evaporated down. 45.8 g (96%) of Z-1-(4-chlorophenyl)-2-hydroxymethyl-4,4-dimethylpent-1-ene are obtained.

Workup

  1. extractionthe resulting emulsion is extracted
  2. stirringby shaking with methylene chloride
  3. customThe organic phase isolated
  4. dry with materialis then dried over sodium sulfate
  5. customevaporated down

Sources & evidence

ORD record
ord-36cd449ac73746d6b9635150252b5d33
Source dataset
uspto-grants-1991_10
Patent number
US05057531

Reaction notes

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