Water → HCID 20394444, compound

HRID 261533Notes

Reaction equation

HRID 261533 reaction equation
[CH2:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5])[CH3:2].[Na].O>CC(CC(C)C)O.C1(C)C=CC=CC=1>[CH2:1]([CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 5360545Sodium2×HCID 53435507HCID 53435507, compound

Product 1

HCID 20394444HCID 20394444, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 79104-Methyl-2-PentanolSolvent

Procedure

A suspension of 91 g of α-ethyl-4-methyl-cinnamic acid in 1.5 liters of methyl-isobutyl-carbinol is added dropwise within one hour to 100 g of sodium in 250 cc of toluene at 130° while stirring well. After a further hour, sodium is no longer present and the mixture is cooled and 500 cc of water are carefully added thereto. The aqueous phase is separated and the methyl-isobutyl-carbinol phase is again extracted twice with water. The entire aqueous phase is acidified with concentrated hydrochloric acid and extracted with ether. The ether extract is washed with water, dried over sodium sulphate and evaporated. The crude α-ethyl-4-methyl-dihydrocinnamic acid is obtained as an oil and may be purified by chromatography.

Workup

  1. waitAfter a further hour
  2. temperaturethe mixture is cooled
  3. customThe aqueous phase is separated
  4. extractionthe methyl-isobutyl-carbinol phase is again extracted twice with water
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washis washed with water
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-756fd31a554747138733b79d62b50836
Source dataset
uspto-grants-1979_08
Patent number
US04166131

Reaction notes

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