Ethanol → HCID 54445106, compound

HRID 1649023Notes

Reaction equation

HRID 1649023 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=C1.[CH2:11]([OH:13])[CH3:12].S(=O)(=O)(O)[OH:15].[OH-].[Na+]>C(OC(=O)C)C>[CH2:11]([O:13][C:2](=[O:1])[CH2:9][C:6]([CH3:7])([CH3:8])[CH2:5][C:4](=[O:15])[CH3:10])[CH3:12]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 6544IsophoroneHCID 14798Sodium Hydroxide

Product 1

HCID 54445106HCID 54445106, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 15.8 g of isophorone in 70.0 g of ethylacetate was ozonolized at 0° C. for 2 hours. After addition of 80.0 g of absolute ethanol and 0.91 g of concentrated sulfuric acid, the reaction solution was cooked overnight under reflux. The cooled solution was adjusted to pH 7 with an ethanolic solution of sodium hydroxide. The ethanol and the ethylacetate were distilled off. The desired 3,3-dimethyl-5-oxo-hexanoic acid ethyl ester was isolated by vacuum distillation. 18.6 g of a colorless fluid (boiling point: 104° to 105° C. at 19 mbar) was obtained which according to gas chromatography contained 98.2 percent of 3,3-dimethyl-5-oxo-hexanoic acid ethyl ester. This corresponds to 18.3 g of 100 percent ester and to a yield of 85.9 percent, calculated on the amount of isophorone used.

Workup

  1. temperatureunder reflux
  2. distillationThe ethanol and the ethylacetate were distilled off

Sources & evidence

ORD record
ord-7724f02f1c3b4124a02b2e12b624d5eb
Source dataset
uspto-grants-1983_11
Patent number
US04414418

Reaction notes

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