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

HRID 917908Notes

Reaction equation

[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

Participants

Conditions

Temperature: 195 °C

Procedure

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##

Workup

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

Sources & evidence

ORD record: ord-cdf5fd5d8d2a4b30b971afb67ac6d4cc
Source dataset: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03968142

Reaction notes

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