Potassium Hydroxide → HCID 21524263, compound

HRID 917912Notes

Reaction equation

HRID 917912 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:18])=[C:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:10]=2)[CH:5]([C:19]([OH:21])=[O:20])[CH2:4][CH2:3]1.O.NN.[OH-].[K+]>C(O)COCCOCCO>[CH:12]1([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][C:8]=2[Cl:18])[CH:5]([C:19]([OH:21])=[O:20])[CH2:4][CH2:3][CH2:2]3)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21524245HCID 21524245, compound

Product 1

HCID 21524263HCID 21524263, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 6 g of 4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid, 4 g of hydrazine hydrate, 6.4 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 and the ethyl acetate is evaporated. The resulting crude product is recrystallized from toluene, to yield 4.5 g of 6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid melting at 119°-120°, of the formula ##SPC10##

Workup

  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 resulting crude product is recrystallized from toluene

Sources & evidence

ORD record
ord-0665af11146a45b4be585f1c6ffa3267
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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