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

HRID 1576214노트

반응식

HRID 1576214 반응식
[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

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 14798Sodium HydroxideHCID 204533371-(3,4-Dimethoxyphenyl)-4-oxocyclohexanecarboxylic Acid2회HCID 21226445Aluminium lithium hydride

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa3ba853a51e4bb7be5439817fbe3128
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03979444

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