Hydrochloric Acid → HCID 13669845, compound

HRID 543406Notes

Reaction equation

HRID 543406 reaction equation
[OH:1][C:2]1[C:15]([CH3:16])=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[Na+].Cl>O.CN(C=O)C>[CH3:16][C:15]1[C:2]([O:1][CH2:25][C:26]([OH:28])=[O:27])=[CH:3][C:4]2[C:5](=[O:17])[C:6]3[C:11]([O:12][C:13]=2[CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617018HCID 15617018, compound

Product 1

HCID 13669845HCID 13669845, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-3-methyl-9-oxo-9H-xanthene (1.1 g), potassium carbonate (1.4 g), ethyl bromoacetate (1.7 g) and DMF (20 ml) was stirred at 60°-70° C. for 3 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 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 DMF gave 1.3 g of 3-methyl-9-oxo-9H-xanthene-2-yloxyacetic acid. m.p. 225°-227° 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 DMF

Sources & evidence

ORD record
ord-060b30ae57204771adc5b2f653d58ae7
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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