Acetic Acid → 6-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([CH:13]1[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH:14]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])#N.C(O)(=[O:32])C>C1C=CC=CC=1.C(OCC)C>[CH:11]([CH:13]1[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH:14]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])=[O:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of diisobutylaluminium hydride (53 g.) in dry benzene (145 ml.) was added, with rapid stirring, to a solution of 7-cyano-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (43.2 g.) in dry diethyl ether (432 ml.) at 10°-15° C. Stirring at ambient temperature was continued for 90 minutes and the mixture was added to 2 N aqueous acetic acid (1 liter) 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 sodium sulphate, the solvents removed in vacuo and the residue distilled under reduced pressure to give 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (25.3 g.), b.p. 164°-200° C.0.05 mm.Hg, νmax 1710 cm-1 , 2700 cm-1 (liquid film).
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 sodium sulphate
- customthe solvents removed in vacuo
- distillationthe residue distilled under reduced pressure
Sources & evidence
- ORD record
- ord-5848d79a2e574352874f03fc2598c6be
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04036872
Reaction notes
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