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

HRID 1581102노트

반응식

HRID 1581102 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7abba9325ac94623b0711108b6030d2e
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03935261

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