1,4-Cyclohexanediol → 4-(Cyclohex-3-enylmethoxy)cyclohexanol

HRID 872427

反応式

HRID 872427 の反応式
Cl[CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1.[CH:9]1([OH:16])[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:3]1([CH2:2][O:15][CH:12]2[CH2:13][CH2:14][CH:9]([OH:16])[CH2:10][CH2:11]2)[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1

参加物

6

反応物 3

HCID 111621,4-CyclohexanediolHCID 14798Sodium HydroxideHCID 5569564-(Chloromethyl)cyclohexene

生成物 1

HCID 667127934-(Cyclohex-3-enylmethoxy)cyclohexanol収率 61.8%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To toluene (500 g) were added 4-chloromethylcyclohexene (0.1 mol), 1,4-cyclohexanediol (0.5 mol), and tetrabutylammonium bromide (0.01 mol), the mixture was raised in temperature to 90° C., and a 5 N NaOH aqueous solution (100 g) was added dropwise thereto, followed by stirring for 5 hours. A toluene solution (toluene layer) was rinsed with water, concentrated, purified by silica gel chromatography, and thereby yielded 13 g of 4-(cyclohex-3-enylmethoxy)cyclohexanol with a purity of 99%.

後処理

  1. washA toluene solution (toluene layer) was rinsed with water
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-52ba03884f7147dc9dc7774e483934c1
出典データセット
uspto-grants-2015_03
特許番号
US08975349B2

関連ノート

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