Acetyl chloride → methyl 7-(6-oxocyclohex-1-enyl)hept-5Z-enoate
Reaction equation
[O:1]=[C:2]1[CH:7]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH2:4][CH2:3]1.[C:17](Cl)(=O)C>CO>[O:1]=[C:2]1[C:7]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH2:5][CH2:4][CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 13.0 g of crude 7-(6-oxocyclohex-2-enyl)hept-5Z-enoic acid in 200 ml of dry methanol was stirred under argon as 2 ml of acetyl chloride was added. The resultant yellow solution was left to stand for 2.6 days (on another occasion 16 hr was found to be sufficient). Solvent was removed by evaporation in vacuo and the residue was dissolved in ether and washed with saturated aqueous sodium bicarbonate. The wash solution was back extracted with ether. The combined ether extracts were dried (MgSO4) and evaporated in vacuo to yield 11.6 g of crude methyl 7-(6-oxocyclohex-1-enyl)hept-5Z-enoate as a yellow oil. This product was purified by chromatography on silicic acid-Celite (85:15) using benzene to ethyl acetate gradient elution to give 0.78 g of ca. 80% pure material and 8.41 g of pure material.
Workup
- additionwas added
- waitThe resultant yellow solution was left
- customon another occasion 16 hr
- customSolvent was removed by evaporation in vacuo
- dissolutionthe residue was dissolved in ether
- washwashed with saturated aqueous sodium bicarbonate
- extractionThe wash solution was back extracted with ether
- dry with materialThe combined ether extracts were dried (MgSO4)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-5fbee133bb7844f9932d88091846372a
- Source dataset
- uspto-grants-1979_04
- Patent number
- US04149017
Reaction notes
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