Hydrochloric Acid → (Z)-2-Hydroxy-6,6-dimethyl-4-oxo-hept-2-enoic acid ethyl ester

HRID 1664230Notes

Reaction equation

HRID 1664230 reaction equation
C([O-])C.[Na+].[CH3:5][C:6]([CH3:12])([CH3:11])[CH2:7][C:8](=[O:10])[CH3:9].[CH2:13]([O:15][C:16](=[O:22])[C:17](OCC)=[O:18])[CH3:14].Cl>CCO.O>[CH2:13]([O:15][C:16](=[O:22])/[C:17](/[OH:18])=[CH:9]/[C:8](=[O:10])[CH2:7][C:6]([CH3:12])([CH3:11])[CH3:5])[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 115464,4-Dimethyl-2-pentanoneHCID 2723922Sodium ethoxide

Product 1

HCID 86626580(Z)-2-Hydroxy-6,6-dimethyl-4-oxo-hept-2-enoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To an ice-cooled solution of sodium ethanolate (128.5 g, 1.79 mol) in EtOH (2500 ml) under nitrogen atmosphere is added 4,4-dimethyl-pentan-2-one (195.0 g, 1.71 mol). Half an hour later, oxalic acid diethyl ester (231.5 g, 1.71 mol) is added. After being stirred at rt for 24 h, the reaction mixture is diluted with water, and acidified to pH 2.0 by 6N aq hydrochloric acid. The mixture is contracted to about 1 L and extracted with DCM. The combined extracts are washed with brine, dried over sodium sulfate, and concentrated in vacuo to yield the product as a brown liquid.

Workup

  1. extractionextracted with DCM
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9b8c97b516f4f6abe498e7885dd6e84
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

Loading…