Hydrochloric Acid → HCID 70046811, compound

HRID 1657253Notes

Reaction equation

HRID 1657253 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 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-373951a91c4242dbb5634680dad7b7b5
Source dataset
uspto-grants-1993_10
Patent number
US05256645

Reaction notes

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