Water → HCID 19972708, compound

HRID 1653804Notes

Reaction equation

HRID 1653804 reaction equation
[O:1]1[CH2:5][CH:2]1[CH2:3]Cl.[OH:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].O>C(O)C>[O:1]1[CH2:5][CH:2]1[CH2:3][O:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 19972623HCID 19972623, compound

Product 1

HCID 19972708HCID 19972708, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7 ml of 2,3-epoxypropyl chloride was added dropwise at 20°-25° C. to a stirred mixture of 5 g of 8-hydroxy-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran and 9.7 ml of 2N sodium hydroxide in 10 ml of ethanol. After 6 hours at 20°-25° C., the reaction mixture was poured into 100 ml of water and the precipitate which formed was collected by suction filtration. After drying and purifying by flash chromatography on silica gel (eluant petroleum ether: ethyl acetate 65:35), there was obtained 4.45 g of the title compound, m.p. 128°-129° C.

Workup

  1. customthe precipitate which formed
  2. filtrationwas collected by suction filtration
  3. customAfter drying
  4. custompurifying by flash chromatography on silica gel (eluant petroleum ether: ethyl acetate 65:35)

Sources & evidence

ORD record
ord-be87f498ea8e418a8a61b168319d03cc
Source dataset
uspto-grants-1995_04
Patent number
US05403842

Reaction notes

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