Hydrochloric Acid → HCID 21268854, compound

HRID 543407Notes

Reaction equation

HRID 543407 reaction equation
Cl[C:2]1[C:15]([OH:16])=[C:14]([Cl:17])[C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+].[ClH:34]>O.CN(C=O)C>[Cl:34][CH:26]([O:16][C:15]1[CH:2]=[CH:3][C:4]2[C:5](=[O:18])[C:6]3[C:11]([O:12][C:13]=2[C:14]=1[Cl:17])=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:27]([OH:29])=[O:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 14663246HCID 14663246, compound

Product 1

HCID 21268854HCID 21268854, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dichloro-3-hydroxy-9-oxo-9H-xanthene (7.5 g), potassium carbonate (7.5 g), ethyl bromoacetate (9.0 g) and DMF (100 ml) was stirred at 55°-65° C. for 3 hours. After cooling the mixture, sodium hydroxide (20 g) and water (250 ml) were added and the resulting mixture was stirred at 90°-100° C. for 1 hour. 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 4.0 g of 2,4-dichloro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 225°-228° 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 1 hour
  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-44b9db511e604f1ab71f6b7c333a6768
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

Loading…