Ethylene Glycol → 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid

HRID 1388822노트

반응식

HRID 1388822 반응식
[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2C(C#N)=[CH:3][CH:2]=1.[OH-:18].[K+].[CH2:20]([OH:23])[CH2:21]O>O>[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:21]([C:20]([OH:23])=[O:18])=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 132813406,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-carbonitrile

생성물 1

HCID 132813416,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

Under a dry nitrogen atmosphere a solution of 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carbonitrile (2.95 grams, 0.0134 mole), potassium hydroxide (4 grams, 0.085 mole), ethylene glycol (40 ml) and water (3 ml) was heated at reflux for approximately 24 hours. The mixture was cooled, diluted with water, and the solution was washed with diethyl ether. The aqueous solution was acidified and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to give a white solid. The solid was combined with similar material prepared in a separate experiment, and the combined solids were recrystallized from n-hexane to give 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid (mp 137°-139°) as nearly white crystals.

후처리

  1. temperatureat reflux for approximately 24 hours
  2. temperatureThe mixture was cooled
  3. washthe solution was washed with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customto give a white solid
  9. customprepared in a separate experiment
  10. customthe combined solids were recrystallized from n-hexane

출처 및 근거

ORD 기록
ord-2328cab52f984d7487b1ab759938b7e6
출처 데이터셋
uspto-grants-1984_02
특허 번호
US04433182

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