Sodium Hydroxide → HCID 53951827, compound

HRID 1658877Notes

Reaction equation

HRID 1658877 reaction equation
C[O:2][C:3](=[O:18])[C:4]([CH3:17])=[CH:5][CH:6]=[CH:7][CH2:8][CH:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14].[OH-].[Na+]>CO.O>[CH3:17][C:4](=[CH:5][CH:6]=[CH:7][CH2:8][CH:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:3]([OH:18])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54097352HCID 54097352, compound

Product 1

HCID 53951827HCID 53951827, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

22.8 g. of 2,7,11-trimethyl-2,4,10-dodecatrienoic acid methyl ester is dissolved in 150 ml of methanol and mixed with 22.8 g. of sodium hydroxide dissolved in 35 ml of water. The mixture is boiled under reflux for 3 hours, poured on to ice-water and extracted with diethyl ether. The ether extracts are discarded and the aqueous phase acidified with dilute sulphuric acid. The acidic aqueous solution is extracted with diethyl ether and the ether extract is washed repeatedly with aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated on a rotary evaporator. There is obtained 2,7,11-trimethyl-2,4,10-dodecatrienoic acid.

Workup

  1. additionmixed with 22.8 g
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with diethyl ether
  4. extractionThe acidic aqueous solution is extracted with diethyl ether
  5. extractionthe ether extract
  6. washis washed repeatedly with aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2780b130f89b4a45a483a51f893ef45e
Source dataset
uspto-grants-1976_06
Patent number
US03966780

Reaction notes

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