Epichlorohydrin → 2,2-Dimethyl-4-(naphthalen-1-yl)-7-[(oxiran-2-yl)methoxy]-2H-1-benzopyran

HRID 224933Notes

Reaction equation

HRID 224933 reaction equation
[CH3:1][C:2]1([CH3:23])[CH:11]=[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:22])=[CH:7][CH:8]=2)[O:3]1.[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:28]1[CH2:27][CH:26]1[CH2:24][O:22][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)=[CH:11][C:2]([CH3:23])([CH3:1])[O:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 233307472,2-Dimethyl-4-(naphthalen-1-yl)-2H-1-benzopyran-7-ol

Product 1

HCID 233307422,2-Dimethyl-4-(naphthalen-1-yl)-7-[(oxiran-2-yl)methoxy]-2H-1-benzopyranYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,2-Dimethyl-4-(1-naphthyl)-2H-chromen-7-ol (7.92 g, 0.026 moles) and epichlorohydrin (28,5 ml) were dissolved in acetone (50 ml). Potassium carbonate (6.3 g), was added and the mixture refluxed for 6 hours, allowed to cool and filtered. The acetone was removed in vacuo and the residue dissolved in ether, washed with water and dried. Removal of solvent gave the title product as an orange oil (8.1 g, 86%) which was used in the next reaction without further purification.

Workup

  1. temperaturethe mixture refluxed for 6 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. customThe acetone was removed in vacuo
  5. dissolutionthe residue dissolved in ether
  6. washwashed with water
  7. customdried
  8. customRemoval of solvent

Sources & evidence

ORD record
ord-94510f9de2ab43b68c833d135e3ac2f3
Source dataset
uspto-grants-1980_11
Patent number
US04234726

Reaction notes

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