Hydrochloric Acid → HCID 13669841, compound

HRID 543404Notes

Reaction equation

HRID 543404 reaction equation
[Cl:1][C:2]1[C:3]([OH:17])=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[Na+].Cl>O.CN(C=O)C>[Cl:1][C:2]1[C:3]([O:17][CH2:25][C:26]([OH:28])=[O:27])=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617016HCID 15617016, compound

Product 1

HCID 13669841HCID 13669841, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chloro-2-hydroxy-9-oxo-9H-xanthene (1.5 g), potassium carbonate (2.5 g), ethyl bromoacetate (3.1 g) and DMF (40 ml) was stirred at 65°-75° C. for 2 hours. After cooling the mixture, sodium hydroxide (4 g) and water (100 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 ethanol gave 1.5 g of 3-chloro-9-oxo9H-xanthene-2-yloxyacetic acid. m.p. 237°-238° C. This compound showed a mass spectrum having a molecular ion peak at m/e 304.

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-0c20e99808e544a3b7d329af560f0a7f
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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