Ethanol → HCID 72683169, compound

HRID 2369284Notes

Reaction equation

HRID 2369284 reaction equation
[OH2:1].[OH-].[K+].[CH3:4][C:5]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:24])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:6][C:7]#N.[CH2:25]([OH:27])C>>[CH3:4][C:5]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:24])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:6][CH2:7][C:25]([OH:27])=[O:1]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 86672625HCID 86672625, compound

Product 1

HCID 72683169HCID 72683169, compound

Conditions

Temperature
80 °C

Procedure

Water (115 mL) and 35.5 g (0.63 mol) of potassium hydroxide were added to a solution of 77 g (0.25 mol) of 3,7,11,15-tetramethylhexadec-2-ene-1-nitrile in ethanol (345 mL). The solution was stirred for 18 hours at 80° C. The reaction mixture was concentrated, and neutralized with 3M hydrochloric acid, and then extracted with ethyl acetate. The extract was washed with saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated to obtain 88 g of 4,8,12,16-tetramethylheptadec-3-enoic acid as a crude product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-40fe0285876442a1b5d8204ae1cc61b7
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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