Hydrochloric Acid → HCID 70046811, compound

HRID 654880Notes

Reaction equation

HRID 654880 reaction equation
[CH2:1]([CH:8]([CH:12]([OH:19])[C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([O-:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([CH:8]([CH:12]([OH:19])[C:13](=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86746008HCID 86746008, compound

Product 1

HCID 70046811HCID 70046811, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 300 mg (1.07 mmol) of the less polar (2R,3R or S)-2-benzyl-3-hydroxy-5,5-dimethyl-4-oxohexanoate and 1.07 ml of 1N sodium hydroxide solution in ml of methanol is stirred at room temperature for hours. Thereafter, the reaction mixture is neutralized with 1.07 ml of 1N hydrochloric acid and evaporated under reduced pressure. The residue is triturated with ethyl acetate and the insoluble solid is separated. After evaporation of the ethyl acetate phase there are obtained 180 mg of (2R,3R or S)-2-benzyl-3-hydroxy-5,5-dimethyl-4-oxohexanoic acid as a colourless solid, MS: 231 (M--CH3 --H2O)+.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue is triturated with ethyl acetate
  3. customthe insoluble solid is separated
  4. customAfter evaporation of the ethyl acetate phase

Sources & evidence

ORD record
ord-d297c6d1d54348d3a96b09967bf5c0ab
Source dataset
uspto-grants-1992_07
Patent number
US05134123

Reaction notes

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