Hydrochloric Acid → HCID 13669828, compound

HRID 1194839Notes

Reaction equation

HRID 1194839 reaction equation
[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[C:9]([F:16])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:19][C:20]([O:22]CC)=[O:21].[OH-].[Na+].Cl>O>[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[C:9]([F:16])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13669827HCID 13669827, compound

Product 1

HCID 13669828HCID 13669828, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.6 g of 4-chloro-8-fluoro-3-hydroxy-9-oxo-9H-xanthene, 2.8 g of postassium carbonate, 3.3. g of ethyl bromoacetate and 40 ml of N,N-dimethylformamide (DMF) was stirred at 60°-70° C. for 4 hours. After cooling the mixture, water was added thereto and the resulting crystal was recovered by filtration, washed with water and dried. Recrystallization from ethanol gave 3.4 g of ethyl 4-chloro-8-fluoro-9-oxo-9H-xanthene-3-yloxyacetate. A mixture of this ester (3.3 g), sodium hydroxide (1.9 g) and water (100 ml) was refluxed for 30 minutes. After cooling, the mixture was rendered acidic with concentrated hydrochloric acid and the resulting crystal was recovered by filtration and dried. Recrystallization from DMF gave 2.5 g of 4-chloro-8-fluoro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 300° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe resulting crystal was recovered by filtration
  4. customdried
  5. customRecrystallization from DMF

Sources & evidence

ORD record
ord-1a7bf8b77a7d41b18bc34bc4c30a8ddb
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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