Water → HCID 21533795, compound

HRID 1657494Notes

Reaction equation

HRID 1657494 reaction equation
[OH-].[K+].C([CH:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:9](=[O:11])[CH3:10])(OCC)=O.S(=O)(=O)(O)O.O>CO>[CH:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:8][C:9](=[O:11])[CH3:10])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 21533810HCID 21533810, compound

Product 1

HCID 21533795HCID 21533795, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.4 g (0.025 mol) of solid potassium hydroxide are dissolved in 30 cc of 50 % aqueous methanol. 4.1 g (0.015 mol) of 3-carbethoxy-9-isopropoxy-2-nonanone are added to this solution and the mixture is heated to boiling temperature. After 1 hour at reflux the reaction mixture is cooled to 50°, neutralized with 50 % sulphuric acid, cooled to room temperature after 10 minutes, and 50 cc of water added. The product is extracted from the heterogeneous mixture with ether, the ether extract is washed with saturated salt solution, dried with sodium sulphate and evaporated. The residue is chromatographed on silica gel with hexane/ethyl acetate 9:1. Pure 9-isopropoxy-2-nonanone is obtained as a colourless oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureAfter 1 hour at reflux the reaction mixture
  3. temperatureis cooled to 50°
  4. extractionThe product is extracted from the heterogeneous mixture with ether
  5. extractionthe ether extract
  6. washis washed with saturated salt solution
  7. dry with materialdried with sodium sulphate
  8. customevaporated
  9. customThe residue is chromatographed on silica gel with hexane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-a82314997aff46968fa3daa1492eb877
Source dataset
uspto-grants-1976_06
Patent number
US03960906

Reaction notes

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