HCID 21524237, compound → HCID 21524245, compound

HRID 917909Notes

Reaction equation

HRID 917909 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH2:18][CH2:19][C:20]([OH:22])=O)[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>S(=O)(=O)(O)O>[O:22]=[C:20]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[C:7]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:6]=2)[CH:14]([C:15]([OH:17])=[O:16])[CH2:18][CH2:19]1

Participants

3

Reactant 1

HCID 21524237HCID 21524237, compound

Product 1

HCID 21524245HCID 21524245, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

While cooling well, 17.9 g of 2-(3-chloro-4-cyclohexylphenyl)-glutaric acid are dissolved in 90 ml of 100% sulfuric acid and the solution is kept overnight at 35°C, then cautiously poured out over ice and the aqueous mixture is extracted with ethyl acetate and evaporated. The remaining crystals are recrystallized from toluene, to yield 12.2 g of 4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid melting at 204°-205°C, of the formula ##SPC8##

Workup

  1. temperatureWhile cooling well
  2. additioncautiously poured out over ice
  3. extractionthe aqueous mixture is extracted with ethyl acetate
  4. customevaporated
  5. customThe remaining crystals are recrystallized from toluene

Sources & evidence

ORD record
ord-ddfc20e179c240bc90ef5ed678cfb004
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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