Boron tribromide → 5-(1,1-Dimethylheptyl)resorcinol

HRID 371608Notes

Reaction equation

[CH3:1][C:2]([C:10]1[CH:15]=[C:14]([O:16]C)[CH:13]=[C:12]([O:18]C)[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].B(Br)(Br)Br>>[CH3:9][C:2]([C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH:11]=1)[OH:18])([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 1089615-(1,1-Dimethylheptyl)-1,3-dimethoxybenzene

Product 1

HCID 918705-(1,1-Dimethylheptyl)resorcinol

Procedure

The process of claim 1, said process comprising reacting 2,6-dimethoxyphenol with 1,1-dimethyl-1-heptanol in the presence of methanesulfonic acid to provide 1-hydroxy-2,6-dimethoxy-4-(1,1-dimethylheptyl)benzene; reacting said 1-hydroxy-2,6-dimethoxy-4-(1,1-dimethylheptyl)benzene with a halogenated disubstituted phosphite to provide a 2,6-dimethoxy-4-(1,1-dimethylheptyl)phenyl disubstituted phosphate; reacting said 2,6-dimethoxy-4-(1,1-dimethylheptyl)phenyl disubstituted phosphate with an alkali metal to afford 1-(1,1-dimethylheptyl)-3,5-dimethoxybenzene; reacting said 1-(1,1-dimethylheptyl)-3,5-dimethoxybenzene with boron tribromide to provide 5-(1,1-dimethylheptyl)-resorcinol, and recovering said 5-(1,1-dimethylheptyl)-resorcinol therefrom.

Sources & evidence

ORD record: ord-8598c00f0e0346b48cbf8083be5426fa
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04087410

Reaction notes

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