1-Phenylcyclohexane-1-carboxylic acid → 1-Phenylcyclohexanemethanol

HRID 1270447

反応式

HRID 1270447 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]2([C:19](O)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[C:7]1([C:13]2([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

3

反応物 2

HCID 708171-Phenylcyclohexane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 1985171-Phenylcyclohexanemethanol収率 89.1%

反応条件

温度
0 °C

実験手順

To a suspension of LAH (3.8 g, 0.1 mol) cooled to 0° C. was slowly added 1-phenyl-cyclohexanecarboxylic acid (10.2 g, 50.0 mmol). After stirring from 0° C. to rt overnight, the reaction mixture was quenched with H2O (3.8 mL), 15% NaOH (3.8 mL), H2O (11.4 mL) and filtered. The salt was washed with Et2O and the combined organic phase dried over anhydrous sodium sulfate to give (1-phenyl-cyclohexyl)-methanol (8.48 g, 89%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.30–1.70 (9H, m), 2.15–2.36 (2H, m), 3.51 (2H, s), 7.20–7.27 (1H, m), 7.34–7.41 (4H, m). Mass Spec [M+H]+=191.1.

後処理

  1. customthe reaction mixture was quenched with H2O (3.8 mL), 15% NaOH (3.8 mL), H2O (11.4 mL)
  2. filtrationfiltered
  3. washThe salt was washed with Et2O
  4. dry with materialthe combined organic phase dried over anhydrous sodium sulfate

出典と根拠

ORDレコード
ord-2966f8321386480fa7fa2921c2d972b8
出典データセット
uspto-grants-2007_04
特許番号
US07202253B2

関連ノート

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