Hydrochloric Acid → HCID 70046811, compound

HRID 274768Notes

Reaction equation

HRID 274768 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-oxo-hexanoate and 1.07 ml of 1N sodium hydroxide solution in 10 ml of methanol is stirred at room temperature for 3 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-bbe4cff33b60419a8e559f21e7353157
Source dataset
uspto-grants-1995_02
Patent number
US05389616

Reaction notes

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