Epichlorohydrin → HCID 13370622, compound

HRID 2412954Notes

Reaction equation

HRID 2412954 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:26])[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11]2)=[CH:6][CH:5]=1.[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>CS(C)=O>[O:31]1[CH2:30][CH:29]1[CH2:27][O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:26])[C:9]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 11833990HCID 11833990, compound

Product 1

HCID 13370622HCID 13370622, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 50% aqueous DMSO (280 ml) containing sodium hydroxide (5.60 g, 140 mmol) was added 7-hydroxy-2,3-diphenylchromone (44.01 g, 140 mmol) and the resultant mixture was stirred until most of the solid went into the solution. Epichlorohydrin was then introduced into the suspension. The solution was stirred at room temperature (RT) for 2.5 days and solid formed during the reaction was collected from time to time (about twice a day). The white solid (total=47.58 g) was recrystallized from isopropyl alcohol several times to afford 28.15 g of relatively pure white prisms, m.p. 143°-145°; yield 54%. The mother liquor was concentrated to produce more crystals.

Workup

  1. customsolid formed during the reaction
  2. customwas collected from time to time (about twice a day)
  3. customThe white solid (total=47.58 g) was recrystallized from isopropyl alcohol several times
  4. customto afford 28.15 g of relatively pure white prisms, m.p. 143°-145°
  5. concentrationThe mother liquor was concentrated
  6. customto produce more crystals

Sources & evidence

ORD record
ord-80ec69bd967b4fd383c19117005730a3
Source dataset
uspto-grants-1985_01
Patent number
US04495198

Reaction notes

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