Acetic Acid → 3-Hydroxy-2-(7-hydroxyheptyl)cyclopentane-1-carbaldehyde

HRID 1581091노트

반응식

HRID 1581091 반응식
[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]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 205429242-(7-Hydroxyheptyl)-3-oxocyclopentanecarbonitrileHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 215614973-Hydroxy-2-(7-hydroxyheptyl)cyclopentane-1-carbaldehyde수율 43%

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매

실험 절차

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.

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
  6. distillationThe residue was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-d2705bb4163b4fce89e06ab71bbba00b
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03935261

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