3-Chloropropiophenone → 3-Chloro-1-phenylpropanol

HRID 1033234Notes

Reaction equation

HRID 1033234 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[BH4-].[Na+]>C(O)C>[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

4

Reactant 2

HCID 702953-ChloropropiophenoneHCID 4311764Sodium borohydride

Product 1

HCID 5720643-Chloro-1-phenylpropanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloropropiophenone (25.2 g) was dissolved in abs. ethanol (200 ml), NaBH4 (2.2 g) was slowly added and the mixture stirred overnight at R.T. The mixture was filtered and the filtrate evaporated to dryness. H2O was added and the solution extracted with ether, the ether phase dried (MgSO4) and evaporated. The resulting oil purified on silicagel CH2Cl2 as eluent giving 3-chloro-1-phenyl-1-propanol (compound 14), identified by 1H NMR.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. additionH2O was added
  4. extractionthe solution extracted with ether
  5. dry with materialthe ether phase dried (MgSO4)
  6. customevaporated
  7. customThe resulting oil purified on silicagel CH2Cl2 as eluent

Sources & evidence

ORD record
ord-67b80f9f702c4f038a3c15d5cb7d607c
Source dataset
uspto-grants-1994_05
Patent number
US05310756

Reaction notes

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