2-Bromoethanol → HCID 13851150, compound

HRID 1194856Notes

Reaction equation

HRID 1194856 reaction equation
[Cl:1][C:2]1[C:15]([OH: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][CH2:26][OH:27]>CN(C=O)C>[Cl:1][C:2]1[C:15]([O:16][CH2:25][CH2:26][OH:27])=[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

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 14663247HCID 14663247, compound

Product 1

HCID 13851150HCID 13851150, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-3-hydroxy-9-oxo-9H-xanthene (8.0 g), potassium carbonate (13 g), 2-bromoethanol (12 g) and DMF (200 ml) was stirred at 45°-55° C. for 3 hours. After distilling off the solvent under vacuum, water was added to the residue and the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from a mixed solvent of DMF and water gave 6.0 g of 2-chloro-3-(2-hydroxyethoxy)-9-oxo-9H-xanthene. m.p. 153°-156° C. This compound produced a mass spectrum having a molecular ion peak at m/e 290.

Workup

  1. distillationAfter distilling off the solvent under vacuum, water
  2. additionwas added to the residue
  3. filtrationthe solid crystal was recovered by filtration
  4. washwashed with water
  5. customdried
  6. customRecrystallization from a mixed solvent of DMF and water

Sources & evidence

ORD record
ord-55bb56667a964c6bbe57a2e6b8c5c660
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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