Potassium Hydroxide → HCID 19880006, compound

HRID 1885118Notes

Reaction equation

HRID 1885118 reaction equation
[OH-].[K+].[CH2:3]([O:8][CH:9]([CH3:24])[CH2:10][CH2:11][CH2:12][CH:13](C(OCC)=O)[C:14]([O:16]CC)=[O:15])[CH2:4][CH2:5][CH2:6][CH3:7]>O>[CH2:3]([O:8][CH:9]([CH3:24])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19880052HCID 19880052, compound

Product 1

HCID 19880006HCID 19880006, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Then, 18.6 g of water was added to 18.6 g of 85% KOH, and under stirring, 25.8 g of the above diester was dropped in 30 min. at 20°-23° C. After the addition, the mixture was stirred for 4 hours at the temperature and extracted with benzene. The benzene layer was washed with 5% NaOH aqueous solution and added to the aqueous layer. The aqueous layer was acidified to pH 1 with 6N-hydrochloric acid and extracted with ether. The ether layer was washed with saturated NaCl aqueous solution and dried, followed by distilling-off of the ether to obtain 21.1 g of a slightly yellowish liquid. The liquid was stirred for 3 hours at 160°-170° C., and after cooling, water was added thereto, followed by extraction with benzene. The benzene layer was washed with 5% NaOH aqueous solution and added to the aqueous layer. The aqueous layer was acidified to pH 1 and extracted with ether, followed by washing with saturated NaCl aqueous solution, drying and distilling-off of the solvent to obtain 14.9 g of 6-pentyloxyheptanoic acid in the form of a yellow liquid.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred for 4 hours at the temperature
  3. extractionextracted with benzene
  4. washThe benzene layer was washed with 5% NaOH aqueous solution
  5. additionadded to the aqueous layer
  6. extractionextracted with ether
  7. washThe ether layer was washed with saturated NaCl aqueous solution
  8. customdried
  9. customto obtain 21.1 g of a slightly yellowish liquid
  10. stirringThe liquid was stirred for 3 hours at 160°-170° C.
  11. temperatureafter cooling
  12. extractionfollowed by extraction with benzene
  13. washThe benzene layer was washed with 5% NaOH aqueous solution
  14. additionadded to the aqueous layer
  15. extractionextracted with ether
  16. washby washing with saturated NaCl aqueous solution
  17. customdrying and distilling-off of the solvent

Sources & evidence

ORD record
ord-6ae83617592f4b38813e99b0f2164b20
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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