Ethanol → HCID 57085192, compound

HRID 2369304Notes

Reaction equation

HRID 2369304 reaction equation
[OH2:1].[OH-].[K+].[CH3:4][C:5]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:6][C:7]#N.[CH2:20]([OH:22])C>>[CH3:4][C:5]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:6][CH2:7][C:20]([OH:22])=[O:1]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 86672632HCID 86672632, compound

Product 1

HCID 57085192HCID 57085192, compound

Conditions

Temperature
80 °C

Procedure

Water (130 mL) and 40 g (0.71 mol) of potassium hydroxide was added to a solution of 67.2 g (285 mmol) of 3,7,11-trimethyldodec-2-ene-1-nitrile in ethanol (470 mL). The solution was stirred for 18 hours at 80° C. After the reaction mixture was concentrated, and then neutralized with concentrated hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate aqueous solution and saturated brine, successively, and dried over sodium sulfate. After filtration, the filtrate was concentrated to obtain 4,8,12-trimethyltridec-3-enoic acid as a crude product.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  4. dry with materialsuccessively, and dried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e91769cb368447e182d4ca29f442f7c3
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

Loading…