Hydrochloric Acid → HCID 21268855, compound

HRID 543408Notes

Reaction equation

HRID 543408 reaction equation
[OH:1][C:2]1[C:3](C)=[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:18](=[O:21])([O-])[O-:19].[K+].[K+].Br[CH2:25][C:26](OCC)=O.[OH-].[Na+].Cl>O.CN(C=O)C>[CH3:25][CH:26]([O:1][C:2]1[CH:3]=[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:18]([OH:19])=[O:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617012HCID 15617012, compound

Product 1

HCID 21268855HCID 21268855, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-hydroxy-2-methyl-9-oxo-9H-xanthene (1.8 g), potassium carbonate (2.2 g), ethyl bromoacetate (2.7 g) and DMF (40 ml) was stirred at 60°-70° C. for 2 hours. After cooling the mixture, sodium hydroxide (3.2 g) and water (40 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 1.8 g of 2-methyl-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 236°-238° C. This compound showed a mass spectrum having a molecular ion peak at m/e 284.

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-48fac4436cc84e8ab6105ecaff36e32b
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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