Sulfuric Acid → Xanthone-2-carboxylic acid

HRID 726769Notes

Reaction equation

HRID 726769 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O>O>[O:13]=[C:11]1[C:6]2[CH:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:19]=[CH:18][C:7]=2[O:8][C:9]2[C:10]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 226650732-(4-Carboxyphenoxy)benzoic acid

Product 1

HCID 473472Xanthone-2-carboxylic acidYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 29.9 g (0.11 mol) of 2-(4-carboxyphenoxy)benzoic acid (Example 10e) and 250 ml of concentrated sulfuric acid is heated at 80° C. for one hour. The resulting solution is then poured onto about 2.5 litres of water and the mixture is stirred vigorously for 30 minutes. The product which has precipitated is filtered off, washed with water and dried under a high vacuum. 23.15 g (85%) of 9-oxo-9H-xanthene-2-carboxylic acid, melting point >280° C., result as a beige powder.

Workup

  1. customThe product which has precipitated
  2. filtrationis filtered off
  3. washwashed with water
  4. customdried under a high vacuum

Sources & evidence

ORD record
ord-6d243c70383e49c49ce727479afd48a6
Source dataset
uspto-grants-1998_01
Patent number
US05710198

Reaction notes

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