Hydrochloric Acid → HCID 13669839, compound

HRID 543403Notes

Reaction equation

HRID 543403 reaction equation
[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:16])[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+].Cl>O.CN(C=O)C>[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:16])[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:26][C:27]([OH:29])=[O:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617007HCID 15617007, compound

Product 1

HCID 13669839HCID 13669839, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,5-dichloro-3-hydroxy-9-oxo-9H-xanthene (2.0 g), potassium carbonate (3.4 g), ethyl bromoacetate (4.2 g) and DMF (60 ml) was stirred at 60°-65° C. for 4 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 DMF gave 1.5 g of 4,5-dichloro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 283°-286° C. This compound gave a mass spectrum having a molecular ion peak at m/e 338.

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-1854c2beb0a94edeb7f5548e959d809e
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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