Acetic Acid → 3-Hydroxy-2-(6-hydroxyhexyl)cyclopentanecarbaldehyde

HRID 1581102Notes

Reaction equation

HRID 1581102 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][CH:18]1[C:22](=[O:23])[CH2:21][CH2:20][CH:19]1[C:24]#N.C(O)(=[O:28])C>C1C=CC=CC=1.C(OCC)C>[OH:23][CH:22]1[CH2:21][CH2:20][CH:19]([CH:24]=[O:28])[CH:18]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][OH:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 21225700DiisobutylaluminumhydrideHCID 215615032-(6-Hydroxyhexyl)-3-oxocyclopentane-1-carbonitrile

Product 1

HCID 215614953-Hydroxy-2-(6-hydroxyhexyl)cyclopentanecarbaldehyde

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of diisobutylaluminum hydride (19.3 g., 0.125 mole) in benzene (170 ml.) was added, with rapid stirring, to a solution of 2-(6-hydroxyhexyl)-3-oxocyclopentanecarbonitrile (8.8 g., 0.042 mole) in dry diethyl ether (200 ml.) at 10°-15°C. Stirring at ambient temperature was continued for 15 minutes and the mixture was added to 2N aqueous acetic acid (170 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 to give crude 3-hydroxy-2-(6-hydroxyhexyl)cyclopentanecarbaldehyde (8.6 g.). It was used without further purification.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. washThe combined organic phases were washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulphate
  5. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-7abba9325ac94623b0711108b6030d2e
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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