Citronellal → HCID 54097352, compound

HRID 1658875Notes

Reaction equation

HRID 1658875 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][CH:7]([CH2:9][CH:10]=O)[CH3:8])[CH3:3].[CH3:12][O:13][C:14](=[O:27])/[C:15](/[CH3:26])=[C:16](\P(OCC)(OCC)=O)/[CH3:17].[Na]>C1C=CC=CC=1.CO>[CH3:12][O:13][C:14](=[O:27])[C:15]([CH3:26])=[CH:16][CH:17]=[CH:10][CH2:9][CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]=[C:2]([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 7794CitronellalHCID 5360545SodiumHCID 86733613HCID 86733613, compound

Product 1

HCID 54097352HCID 54097352, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

24 g of citronellal and 40 g of diethylphosphono-α-methylcrotonic acid methyl ester are dissolved in 100 ml of absolute benzene. To this solution there is added dropwise 4 g of sodium in 50 ml of absolute methanol. The mixture is stirred for 5 hours at 60°C., poured on to ice-water and extracted with diethyl ether. The ethereal solution is washed with water, then with aqueous sodium bicarbonate solution and once again with water, dried over sodium sulphate, filtered and concentrated on a rotary evaporator. After chromatography on a 30-fold amount of Kieselgel, using hexane/diethyl ether (9:1 parts by volume) as the eluant, there is obtained 2,7,11-trimethyl-2,4,10-dodecatrienoic acid methyl ester; boiling point 95°C/0.001 mmHg.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ethereal solution is washed with water
  3. dry with materialwith aqueous sodium bicarbonate solution and once again with water, dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-26fae241d2fb4826bd89a1beb789d435
Source dataset
uspto-grants-1976_06
Patent number
US03966780

Reaction notes

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