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

HRID 1581102ノート

反応式

HRID 1581102 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7abba9325ac94623b0711108b6030d2e
出典データセット
uspto-grants-1976_01
特許番号
US03935261

反応ノート

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