Benzene → 3-(2-oxocyclododecyl)propanoic acid
Reaction equation
[C:1]([CH:6]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:18])(OCC)=O.[C:19]1(=[O:23])[O:22]C[CH2:20]1.C1C=CC=CC=1.[H-].[Na+]>C(OCC)C.C1(C)C=CC=CC=1>[O:18]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:6]1[CH2:1][CH2:20][C:19]([OH:23])=[O:22]Participants
7
Procedure
The inventors have established a more effective method for producing β-(2-oxocyclododecyl)propionic acid by the following steps: reacting cyclododecanone with diethyl carbonate to give carbethoxycyclododecanone, reacting the carboethoxycyclododecanone with β-propiolactone in a solvent having no alkoxy group, such as benzene, toluene and ethyl ether in the presence of sodium hydride, hydrolyzing the resulting product, and then decarboxylating to give β-(2-oxocyclododecyl)propionic acid in high yield (79% based on the starting cyclododecanone theoretically).
Sources & evidence
- ORD record
- ord-4e86e0d1149641c5adc5946b1cf76a01
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04005107
Reaction notes
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