Potassium Hydroxide → 1-Methyl-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

HRID 917908노트

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HRID 917908 반응식
[CH3:1][C:2]1([C:20]([OH:22])=[O:21])[C:11]2[C:6](=[CH:7][C:8]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[C:9]([Cl:12])[CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.O.NN.[OH-].[K+]>C(O)COCCOCCO>[CH3:1][C:2]1([C:20]([OH:22])=[O:21])[C:11]2[C:6](=[CH:7][C:8]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[C:9]([Cl:12])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 215242541-Methyl-4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

생성물 1

HCID 215242561-Methyl-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid수율 92.1%

시약·촉매·용매 1

HCID 8172Triethylene Glycol용매

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온도
195 °C

실험 절차

A mixture of 6.7 g of 1-methyl-4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid, 4 g of hydrazine hydrate, 6.7 g of potassium hydroxide and 40 ml of triethyleneglycol is heated for 2 hours at 130°-140°C. Then, while distilling off a mixture of hydrazine and water, the temperature is raised to 195°C and the batch is stirred until nitrogen is no longer being given off, then diluted with 50 ml of water, acidified with concentrated hydrochloric acid and the mixture is extracted with ethyl acetate. The ethyl acetate is evaporated and the residual crude product recrystallized from acetone, to yield 5.9 g of 1-methyl-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid melting at 167°-168°C, of the formula ##SPC7##

후처리

  1. temperatureis heated for 2 hours at 130°-140°C
  2. distillationThen, while distilling off
  3. additiona mixture of hydrazine and water
  4. additiondiluted with 50 ml of water
  5. extractionthe mixture is extracted with ethyl acetate
  6. customThe ethyl acetate is evaporated
  7. customthe residual crude product recrystallized from acetone

출처 및 근거

ORD 기록
ord-cdf5fd5d8d2a4b30b971afb67ac6d4cc
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03968142

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