Toluene → HCID 54352724, compound

HRID 1165615Notes

Reaction equation

HRID 1165615 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15](=[CH:17][CH2:18][CH2:19][CH:20](CC=O)[CH3:21])[CH3:16].C1(C)C=CC=CC=1>O>[C:5]([O:4][CH:1]=[CH:2][CH:20]([CH3:21])[CH2:19][CH2:18][CH:17]=[C:15]([CH3:16])[CH3:14])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7794CitronellalHCID 7918Acetic AnhydrideHCID 11430Potassium Carbonate

Product 1

HCID 54352724HCID 54352724, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

167 kg of acetic anhydride and 77 kg of potassium carbonate were heated to 80° in a reaction vessel equipped with an introduction pump and a condenser. 85 kg of (±)-citronellal were then added by means of the introduction pump during 40 min and the mixture was refluxed for 7 hours. After cooling, 100 kg of toluene and 500 l of water were added thereto and after separation of the organic phase the mixture was washed with 100 l of water to give a solution of 3,7-dimethyl-octa-1,6-dien-l-yl acetate in toluene accompanied by minor quantities of a diester of formula ##STR8##

Workup

  1. customequipped with an introduction pump and a condenser
  2. temperaturethe mixture was refluxed for 7 hours
  3. temperatureAfter cooling
  4. customafter separation of the organic phase the mixture
  5. washwas washed with 100 l of water

Sources & evidence

ORD record
ord-ef6f1564de9640d7be6e8813dd9287b1
Source dataset
uspto-grants-1990_03
Patent number
US04910347

Reaction notes

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