Epichlorohydrin → HCID 13565336, compound

HRID 2119077Notes

Reaction equation

HRID 2119077 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:13]2[C:12]3[CH2:14][CH2:15][CH2:16][CH2:17][C:11]=3[C:10](=[O:18])[O:9][C:8]=2[CH:7]=[C:6]([CH3:19])[CH:5]=1.[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl>CS(C)=O.O>[CH3:19][C:6]1[CH:5]=[C:4]([O:3][CH2:20][CH:22]2[CH2:23][O:24]2)[C:13]2[C:12]3[CH2:14][CH2:15][CH2:16][CH2:17][C:11]=3[C:10](=[O:18])[O:9][C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 5349665HCID 5349665, compound

Product 1

HCID 13565336HCID 13565336, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of NaOH (4.0 g. 0.1 mol) in dimethylsulfoxide (DMSO) (250 ml) and water (250 ml), was added 7,8,9,10-tetrahydro-1-hydroxy-3-methyl-6-oxo-6H-dibenzo[b,d]pyran (20.0 g. 0.087 mol) and the mixture stirred for 5 minutes, then treated with epichlorohydrin (50 ml). After 5 hours the mixture was cooled in a ice bath for 30 minutes and the precipitated solid collected by filtration, washed with water and dried to give 7,8,9,10-tetrahydro-3-methyl-1-(oxiranylmethoxy)-6-oxo-6H-dibenzo[b,d]pyran as a white solid, m.p. 164°-165° C. An analytical sample recrystallized from methanol melted at 165°-166° C.

Workup

  1. temperatureAfter 5 hours the mixture was cooled in a ice bath for 30 minutes
  2. filtrationthe precipitated solid collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ad74c2766f8a49cfafa96562e5c94165
Source dataset
uspto-grants-1987_07
Patent number
US04681954

Reaction notes

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