Hydrochloric Acid → 2,7-Dichloro-9H-xanthene-9-carboxylic acid

HRID 2373079Notes

Reaction equation

HRID 2373079 reaction equation
[CH:1]1[C:14]2[CH:13]([C:15]([OH:17])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:18]N1C(=O)CCC1=O.[ClH:26]>C(O)(=O)C>[Cl:26][C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[C:12](=[CH:11][C:10]([Cl:18])=[CH:9][CH:8]=3)[CH:13]([C:15]([OH:17])=[O:16])[C:14]=2[CH:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 65736Xanthene-9-carboxylic acid

Product 1

HCID 232831092,7-Dichloro-9H-xanthene-9-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 10 g of xanthene-9-carboxylic acid and 14 g of N-chlorosuccinimide in 80 mL of acetic acid was added with stirring dropwise 2.0 mL of conc. HCl over a period of 5 minutes. The mixture was stirred at room temperature for 12 hours and quenched by the addition of 150 mL of water. The precipitated solid was removed by filtration, rinsed with water, and dried in air to give 12.6 g (100%) of the crude carboxylic acid as a white solid. Recrystallization from MeOH--EtOAc (2:1) gave 6.98 g (55.2%) of the pure 2,7-dichloroxanthene-9-carboxylic acid as colorless small needles, m.p. 273°-275° C. (dec.); IR (KBr): 2970 (b, OH), 1695 (C=O) cm-1 ; 1H NMR (DMSO-d6): δ 5.01 s, 1H, CH), 7.05-7.50 (m, 6H, aryl).

Workup

  1. additionwas added
  2. customquenched by the addition of 150 mL of water
  3. customThe precipitated solid was removed by filtration
  4. washrinsed with water
  5. customdried in air

Sources & evidence

ORD record
ord-f27e2c0a0097499ea4991674c86ad472
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

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