p-Toluenesulfonic acid → 4,8,12-Trimethyltrideca-3,7,11-trien-2-one
Reaction equation
[O:1]=[C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])[CH3:3].[CH3:8][C:9](=[CH:11][CH2:12][CH2:13]/[C:14](=[CH:16]/[CH2:17]O)/[CH3:15])[CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[CH3:6][C:5]([CH2:7][CH2:17][CH:16]=[C:14]([CH3:15])[CH2:13][CH2:12][CH:11]=[C:9]([CH3:10])[CH3:8])=[CH:4][C:2](=[O:1])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
A mixture of 200 parts of mesityl oxide, 200 parts of geraniol and 400 parts of tetrahydrofuran has 0.01 part of p-toluenesulfonic acid added to it and the whole is heated for 3 hours at 200°C at 50 atmospheres pressure. The reaction mixture is distilled and 133 parts of 4,8,12-trimethyl-3,7,11-tridecatrien-2-one is obtained. At a conversion of 52% the yield is 78% of theory based on geraniol.
Workup
- additionadded to it
- distillationThe reaction mixture is distilled
Sources & evidence
- ORD record
- ord-8433bca42a5e4ebf86c9764de0b429bb
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03954804
Reaction notes
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