Epichlorohydrin → 7-(2,3-Epoxypropoxy)-2,2-dimethyl-4-phenylchroman

HRID 224920

Reaction equation

HRID 224920 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>CC(C)=O>[O:30]1[CH2:29][CH:28]1[CH2:26][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 205705312,2-Dimethyl-7-hydroxy-4-phenylchroman

Product 1

HCID 233307567-(2,3-Epoxypropoxy)-2,2-dimethyl-4-phenylchromanYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-hydroxy-2,2-dimethyl-4-phenylchroman (11.8 g, 0.046 mole), anhydrous potassium carbonate (11.7 g, 0.093 mole), epichlorohydrin (50 ml) and dry acetone (50 ml) was stirred and boiled under reflux for 6 hours, then cooled and filtered. The filtrate was evaporated in vacuo and the residual brown oil dissolved in ether, washed with water and dried (magnesium sulphate). Removal of the solvent gave 7-(2,3-epoxypropoxy)-2,2-dimethyl-4-phenylchroman as a pale brown solid (13.56 g, 95%), m.p. 82°-85°, after crystallisation from ethanol.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. dissolutionthe residual brown oil dissolved in ether
  6. washwashed with water
  7. dry with materialdried (magnesium sulphate)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-fa6fa54be04d46ee86d2338b7d31e054
Source dataset
uspto-grants-1980_11
Patent number
US04234726

Linked notes

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