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

HRID 838908

Reaction equation

HRID 838908 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 (7.92g, 0.026 moles) and epichlorohydrin (28.5ml) were dissolved in acetone (50ml). Potassium carbonate (6.3g) 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 (8.1g, 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-4871d60601414ac78158ac2981ebf75f
Source dataset
uspto-grants-1978_06
Patent number
US04093631

Linked notes

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