HCID 12952211, compound → HCID 12952222, compound

HRID 1577990Notes

Reaction equation

HRID 1577990 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=C(C#N)[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2.O.S(=O)(=O)(O)O.[C:24]([OH:27])(=[O:26])[CH3:25]>O>[O:1]=[C:2]1[C:15]2[CH:14]=[C:25]([C:24]([OH:27])=[O:26])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2

Participants

4

Reactant 2

HCID 12952211HCID 12952211, compoundHCID 86597087Acetic acid sulfuric acid water

Product 1

HCID 12952222HCID 12952222, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 88.0 g of 5,6,7,8-tetrahydro-9-oxo-xanthene-2-carbonitrile obtained in Example 12 was added 1.5 l of a mixed solution of water-sulfuric acid-acetic acid (1:1:1), and the mixture was heated for 2 hours under refluxing and stirring conditions. After being cooled, the reaction mixture was combined with 1.5 l of water and then ice-cooled for 2 hours. The resulting crystal deposit was collected by filtration, washed with water and then air-dried. The deposit was recrystallized from acetic acid to obtain 84.9 g (yield: 88.5%) of 5,6,7,8-tetrahydro-9-oxo-xanthene-2-carboxylic acid as light yellowish prism-like crystals having a melting point of 253° to 255° C.

Workup

  1. temperaturethe mixture was heated for 2 hours
  2. temperatureunder refluxing
  3. temperatureAfter being cooled
  4. temperatureice-cooled for 2 hours
  5. filtrationThe resulting crystal deposit was collected by filtration
  6. washwashed with water
  7. customair-dried
  8. customThe deposit was recrystallized from acetic acid

Sources & evidence

ORD record
ord-1c0e606d518541828bc0cb5006905293
Source dataset
uspto-grants-1981_09
Patent number
US04290954

Reaction notes

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