Hydrochloric Acid → HCID 13669831, compound

HRID 1194843Notes

Reaction equation

HRID 1194843 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([OH:17])=[CH:9][C:8]=1[O:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[Na+].Cl>O.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([O:17][CH2:25][C:26]([OH:28])=[O:27])=[CH:9][C:8]=1[O:7]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617001HCID 15617001, compound

Product 1

HCID 13669831HCID 13669831, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.8 g of 8-fluoro-3-hydroxy-9-oxo-9H-xanthene, 3.2 g of potassium carbonate, 3.7 g of ethyl bromoacetate and 100 ml of DMF was stirred at 60°-70° C. for 4 hours. After cooling the mixture, 5 g of sodium hydroxide and 100 ml of water were added, and the resulting mixture was stirred at 90°-100° C. for 30 minutes. After cooling, the mixture was rendered acidic with hydrochloric acid and the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from ethanol gave 2.0 g of 8-fluoro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 180°-183° C. This compound showed a mass spectrum having a molecular ion peak at m/e 288.

Workup

  1. additionwere added
  2. stirringthe resulting mixture was stirred at 90°-100° C. for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe solid crystal was recovered by filtration
  5. washwashed with water
  6. customdried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-f43ea77759d84993866d5dbf7ac7d335
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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