HCID 21524262, compound → 1-Methyl-4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

HRID 917907Notes

Reaction equation

HRID 917907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:5]([CH2:10][CH2:11][C:12](O)=[O:13])([CH3:9])[C:6]([OH:8])=[O:7]>S(=O)(=O)(O)O>[CH3:9][C:5]1([C:6]([OH:8])=[O:7])[C:4]2[C:15](=[CH:16][C:17]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)=[C:2]([Cl:1])[CH:3]=2)[C:12](=[O:13])[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 21524262HCID 21524262, compound

Product 1

HCID 215242541-Methyl-4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

With thorough cooling 13.6 g of 3-chloro-4-cyclohexyl-α-(2-carboxyethyl)-hydratropic acid are dissolved in 70 ml of 100% sulfuric acid and the solution is kept over-night at room temperature, then cautiously poured out over ice and the aqueous mixture is extracted with ethyl acetate and the extract is evaporated. The resulting crystals are recrystallized from acetone, to yield 11.5 g of 1-methyl-4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid, melting at 227°-228°C, of the formula ##SPC5##

Workup

  1. waitthe solution is kept over-night at room temperature
  2. additioncautiously poured out over ice
  3. extractionthe aqueous mixture is extracted with ethyl acetate
  4. customthe extract is evaporated
  5. customThe resulting crystals are recrystallized from acetone

Sources & evidence

ORD record
ord-ac6e5aa4855c4022aee35b85781ac13d
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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