Acetic Acid → 3-Hydroxy-2-(7-hydroxyheptyl)cyclopentane-1-carbaldehyde
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[C:23](=[O:24])[CH2:22][CH2:21][CH:20]1[C:25]#N.C(O)(=[O:29])C>C1C=CC=CC=1.C(OCC)C>[OH:24][CH:23]1[CH2:22][CH2:21][CH:20]([CH:25]=[O:29])[CH:19]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][OH:11]Participants
Procedure
A solution of diisobutylaluminium hydride (25.6 g., 0.18 mole) in benzene (250 ml.) was added, with rapid stirring, to a solution of 2-(7-hydroxyheptyl)-3-oxocyclopentanecarbonitrile (10 g., 0.045 mole) in dry diethyl ether (250 ml.) at 10°-15°C. Stirring at ambient temperature was contined for 15 minutes and the mixture was added to 2N aqueous acetic acid (300 ml.) at a temperature lower than 15°C. The organic phase was separated and the aqueous layer was extracted with diethyl ether. The combined organic phases were washed with aqueous sodium bicarbonate, dried over magnesium sulphate and the solvents were removed in vacuo. The residue was distilled under reduced pressure to give 3-hydroxy-2-(7-hydroxyheptyl)cyclopentanecarbaldehyde (4.5 g., 43%), b.p. 185°-193°C./0.1 mm.Hg, nD22.5 1.4995.
Workup
- customThe organic phase was separated
- extractionthe aqueous layer was extracted with diethyl ether
- washThe combined organic phases were washed with aqueous sodium bicarbonate
- dry with materialdried over magnesium sulphate
- customthe solvents were removed in vacuo
- distillationThe residue was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-d2705bb4163b4fce89e06ab71bbba00b
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03935261
Reaction notes
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