2-Bromomethylnaphthalene → 4-Methoxy-2,6-dimethyl-4-[3-(naphth-2-ylmethoxy)phenyl]tetrahydropyran

HRID 2372485Notes

Reaction equation

Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[OH:13][C:14]1[CH:15]=[C:16]([C:20]2([O:28][CH3:29])[CH2:25][CH:24]([CH3:26])[O:23][CH:22]([CH3:27])[CH2:21]2)[CH:17]=[CH:18][CH:19]=1>>[CH3:29][O:28][C:20]1([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH2:2][C:3]3[CH:12]=[CH:11][C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=3)[CH:15]=2)[CH2:25][CH:24]([CH3:26])[O:23][CH:22]([CH3:27])[CH2:21]1

Participants

Reactant 2

HCID 703202-Bromomethylnaphthalene

HCID 200806184-(3-Hydroxyphenyl)-4-methoxy-2,6-dimethyltetrahydropyran

Product 1

HCID 200805934-Methoxy-2,6-dimethyl-4-[3-(naphth-2-ylmethoxy)phenyl]tetrahydropyranYield 92%

Procedure

Using the procedure described in Example 5, 2-bromomethylnaphthalene (0.234 g) was reacted with 4-(3-hydroxyphenyl)-4-methoxy-2,6-dimethyltetrahydropyran (0.2 g, less polar isomer) to give 4-methoxy-2,6-dimethyl-4-[3-(naphth-2-ylmethoxy)phenyl]tetrahydropyran (0.29 g, 92%), m.p. 105°-107° C.

Sources & evidence

ORD record: ord-20fe286057ef4a168dcaa71420e67b3e
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098930

Reaction notes

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