Hydrochloric Acid → HCID 13669832, compound

HRID 543397Notes

Reaction equation

HRID 543397 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])=[C:9]([CH3:18])[C:8]=1[O:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[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][CH2:26][C:27]([OH:29])=[O:28])=[C:9]([CH3:18])[C:8]=1[O:7]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617002HCID 15617002, compound

Product 1

HCID 13669832HCID 13669832, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g of 8-fluoro-3-hydroxy-4-methyl9-oxo-9H-xanthene, 3.0 g of potassium carbonate, 3.6 g of ethyl bromoacetate and 40 ml of DMF was stirred at 60°-70° C. for 2 hours. After cooling the mixture, sodium hydroxide (3 g) and water (40 ml) 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 DMF gave 1.4 g of 8-fluoro-4-methyl-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 259°-261° C. This compound showed a mass spectrum having a molecular ion peak at m/e 302.

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 DMF

Sources & evidence

ORD record
ord-e07ccdb9c64948689d3d9293375ba669
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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