HCID 20367026, compound → HCID 20367021, compound

HRID 616967Notes

Reaction equation

HRID 616967 reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([CH3:18])[CH2:14][C:15]([OH:17])=O)=[CH:7][CH:6]=1)([OH:3])=[O:2]>O>[CH3:18][CH:13]1[CH2:14][C:15](=[O:17])[C:9]2[CH:10]=[C:5]([CH2:4][C:1]([OH:3])=[O:2])[CH:6]=[CH:7][C:8]=2[CH2:11][CH2:12]1

Participants

3

Reactant 1

HCID 20367026HCID 20367026, compound

Product 1

HCID 20367021HCID 20367021, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.8 g of 5-(4-carboxymethylphenyl)-3-methylvaleric acid are added at 100°, while stirring, to 200 g of polyphosphoric acid. The reaction mixture is stirred at 100° for a further hour, is cooled to about 60°, and 100 cc of water are added dropwise thereto. The reaction mixture is then poured on ice, extracted with methylene chloride, the methylene chloride extract is washed with water and dried over sodium sulphate. The 6,7,8,9-tetrahydro-7-methyl-9-oxo-5H-benzocycloheptene-2-acetic acid, obtained after concentrating the solvent, is purified by chromatography on silica gel. The title compound has a M.P. of 105°-107° (from acetonitrile). The cyclohexylammonium salt form of the title compound has a M.P. of 135°-137° (from acetonitrile).

Workup

  1. temperatureis cooled to about 60°
  2. additionThe reaction mixture is then poured on ice
  3. extractionextracted with methylene chloride
  4. extractionthe methylene chloride extract
  5. washis washed with water
  6. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-d0a740f15b3a4aeb82ae71d41fc3dd29
Source dataset
uspto-grants-1978_02
Patent number
US04076838

Reaction notes

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