Heptanoic acid, 6-oxo-, methyl ester → Methyl 6-hydroxyheptanoate

HRID 1926890Notes

Reaction equation

HRID 1926890 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:10])[CH3:9].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([OH:10])[CH3:9]

Participants

4

Reactant 2

HCID 288022Heptanoic acid, 6-oxo-, methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 13085553Methyl 6-hydroxyheptanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Put 10 g (63.2 mmol) 6-oxo-heptanoic acid methyl ester in 50 ml methanol. Add, in portions, 1.196 g (31.6 mmol) sodium borohydride. After the exothermic reaction has subsided, stir for a further 30 min under reflux. Then concentrate by evaporation. Take up the residue in water, acidify with 1 M hydrochloric acid and extract twice with dichloromethane. Dry the organic phases and concentrate by evaporation. 7.9 g (78.0% of theor.) of the target compound is obtained.

Workup

  1. customAfter the exothermic reaction
  2. temperatureunder reflux
  3. concentrationThen concentrate by evaporation
  4. extractionextract twice with dichloromethane
  5. customDry the organic phases
  6. concentrationconcentrate by evaporation
  7. custom7.9 g (78.0% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-19fbe52085074dc0af204769a1d1e72d
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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