1-Propanol → HCID 22759335, compound

HRID 329303Notes

Reaction equation

HRID 329303 reaction equation
[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]1[O:21][CH2:20]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])(=[O:3])[CH3:2].[CH2:22]([OH:25])[CH2:23][CH3:24].[OH-].[Na+]>O>[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([OH:21])[CH2:20][O:25][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 14798Sodium HydroxideHCID 22759269HCID 22759269, compound

Product 1

HCID 22759335HCID 22759335, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of ethyl 8-acetyl-12,13-epoxytridecanoate (14.9 g., 0.05 mole), propanol (60 ml.), sodium hydroxide (6.0 g., 0.15 mole) and water (15 ml.) is stirred 4 hours at 40°-45° and then heated 1 hour on the steam bath. The mixture is cooled, treated with water (250 ml.) and extracted with ether. The aqueous solution is acidified with hydrochloric acid. The oily product is taken up in ether, washed with water, and dried over sodium sulfate. Evaporation of the ether leaves the title compound as a pale yellow oil. Purification is effected by column chromatography on silica gel with 2% methanol in chloroform as the eluant.

Workup

  1. temperatureheated 1 hour on the steam bath
  2. temperatureThe mixture is cooled
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the ether

Sources & evidence

ORD record
ord-6c4ebde4178c45dd971410743b2cafa5
Source dataset
uspto-grants-1977_04
Patent number
US04020177

Reaction notes

Loading…