Lithium Hydroxide → 4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

HRID 349099

反応式

HRID 349099 の反応式
[CH:1]1([C:11]([O:13]C)=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:10][O:9][C:7]([CH:4]1[CH2:5][CH2:6][CH:1]([C:11]([OH:13])=[O:12])[CH2:2][CH2:3]1)=[O:8]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 7198Dimethyl 1,4-cyclohexanedicarboxylate

生成物 1

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acid収率 77.9%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

To a stirred solution of dimethyl cyclohexane-1,4-dicarboxylate (10.2 g, 51 mmol) in a mixture of 2:1:1 tetrahydrofuran/methanol/water (52 mL) was added lithium hydroxide (2.13 g, 51 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between diethyl ether and water. The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid, and the precipitate collected, and dried under vacuum to afford 4-(methoxycarbonyl)cyclohexanecarboxylic acid (7.4 g): 1H NMR (300 MHz, CDCl3) δ 3.68 (s, 3H), 2.33–2.27 (m, 2H), 2.11–2.06 (m, 4H), 1.50–1.43 (m, 4H).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between diethyl ether and water
  3. customthe precipitate collected
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-43304f0fdc8f4b1eb1d65be76a622463
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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