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

HRID 224925Notes

Reaction equation

HRID 224925 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:18])=[CH:7][CH:8]=2)[O:3]1.[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl>>[O:24]1[CH2:23][CH:22]1[CH2:20][O:18][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][C:2]([CH3:19])([CH3:1])[O:3]2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 7835EpichlorohydrinHCID 205704922,2-Dimethyl-4-phenyl-2H-1-benzopyran-7-ol

Product 1

HCID 233307482,2-Dimethyl-7-[(oxiran-2-yl)methoxy]-4-phenyl-2H-1-benzopyranYield 78%

Procedure

Reaction of 2,2-dimethyl-4-phenyl-2H-chromen-7-ol with epichlorohydrin, by an analogous process to that described in Example 1 gave 7-(2,3-epoxypropoxy)-2,2-dimethyl-4-phenyl-2H-chromene (78%). Reaction of this epoxide with dimethylamine by an analogous process to that described in Example 2 gave 7-(2-hydroxy-3-dimethylaminopropoxy)-2,2-dimethyl-4-phenyl-2H-chromene isolated as its hydrochloride salt (48%), m.p. 208°-209°.

Sources & evidence

ORD record
ord-4a0cfd15279f45029240991995d29c53
Source dataset
uspto-grants-1980_11
Patent number
US04234726

Reaction notes

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