Sodium → HCID 13771307, compound

HRID 2107136Notes

Reaction equation

HRID 2107136 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:18])[C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1>C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:18])[C:15]([OH:17])=[O:16])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 230477547-(4-Chlorophenyl)-2-oxoheptanoic acid

Product 1

HCID 13771307HCID 13771307, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1.84 g (48.6 mmol) of sodium hydroboride in 175 ml of ethanol is added rapidly, with stirring, to a solution of 11.25 g (44 mmol) of 7-(4-chlorophenyl)-2-oxoheptanoic acid in 175 ml of ethanol at 50° C. Then the mixture is let stand for 3 hours at room temperature, the reaction mixture is concentrated, and the residue is dissolved with water. After acidification the aqueous phase is extracted with acetic ester. The organic extracts are dried and concentrated. The residual oil is dissolved in aqueous sodium hydrogen carbonate solution, the solution is clarified with charcoal, and the oil that separates after acidification is dissolved with ether. By concentrating the dried ether solution, 7.4 g is obtained (65% of theory) of 7-(4-chlorophenyl)-2-hydroxyheptanoic acid, M.P. 78°-81° C.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. dissolutionthe residue is dissolved with water
  3. extractionAfter acidification the aqueous phase is extracted with acetic ester
  4. customThe organic extracts are dried
  5. concentrationconcentrated
  6. dissolutionThe residual oil is dissolved in aqueous sodium hydrogen carbonate solution
  7. dissolutionthe oil that separates after acidification is dissolved with ether
  8. concentrationBy concentrating the dried ether solution

Sources & evidence

ORD record
ord-31d52b9d745c4b4e814bc964f1bb01f0
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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