Tetrahydrofuran → 4-(3,4-Dimethoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one

HRID 1576214ノート

反応式

HRID 1576214 の反応式
[C:1]([C:4]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)(O)=[O:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:2][CH2:1][C:4]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 14798Sodium HydroxideHCID 204533371-(3,4-Dimethoxyphenyl)-4-oxocyclohexanecarboxylic Acid2 回HCID 21226445Aluminium lithium hydride

生成物 1

HCID 215146714-(3,4-Dimethoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one収率 62.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A solution of 19 g. (0.059 mole) of 4-carboxy-4-(3,4-dimethoxyphenyl)cyclohexanone, ethylene ketal (prepared in Example 28) in 290 ml. of tetrahydrofuran is added to 5.35 g. (0.141 mole) lithium aluminum hydride in 80 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux the mixture is cooled in ice and treated successively with 5.4 ml. of water, 5.4 ml. of 15% sodium hydroxide solution and 16.2 ml. of water. The resulting inorganic gel is collected on a filter and rinsed with ether. The combined filtrates are evaporated to dryness to give 11.4 g. (62.7% yield) of 4-hydroxymethyl-4-(3,4-dimethoxyphenyl)-cyclohexanone, ethylene ketal as an amorphous gum.

後処理

  1. temperatureof heating
  2. temperatureat reflux the mixture
  3. temperatureis cooled in ice
  4. additiontreated successively with 5.4 ml
  5. customThe resulting inorganic gel is collected on
  6. filtrationa filter
  7. washrinsed with ether
  8. customThe combined filtrates are evaporated to dryness
  9. customto give 11.4 g

出典と根拠

ORDレコード
ord-aa3ba853a51e4bb7be5439817fbe3128
出典データセット
uspto-grants-1976_09
特許番号
US03979444

反応ノート

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