4-Bromomethylphthalic acid dimethyl ester → (E)-7-[3-(3,4-bis-Hydroxymethylbenzyloxy)phenyl]-3-ethyloct-6-en-3-ol

HRID 2120476Notes

Reaction equation

HRID 2120476 reaction equation
[CH2:1]([C:3]([OH:18])([CH2:6][CH2:7]/[CH:8]=[C:9](/[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1)\[CH3:10])[CH2:4][CH3:5])[CH3:2].Br[CH2:20][C:21]1[CH:22]=[C:23]([C:31](OC)=[O:32])[C:24](=[CH:29][CH:30]=1)[C:25](OC)=[O:26]>>[OH:32][CH2:31][C:23]1[CH:22]=[C:21]([CH:30]=[CH:29][C:24]=1[CH2:25][OH:26])[CH2:20][O:17][C:13]1[CH:12]=[C:11](/[C:9](/[CH3:10])=[CH:8]/[CH2:7][CH2:6][C:3]([CH2:4][CH3:5])([OH:18])[CH2:1][CH3:2])[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 232556044-Bromomethylphthalic acid dimethyl esterHCID 23439826(E)-3-ethyl-7-(3-hydroxyphenyl)oct-6-en-3-ol

Product 1

HCID 67533486(E)-7-[3-(3,4-bis-Hydroxymethylbenzyloxy)phenyl]-3-ethyloct-6-en-3-olYield 84.3%

Procedure

In a manner similar to Example 64(d), by reacting 112 mg (0.39 mmol) of (E)-3-ethyl-7-(3-hydroxyphenyl)oct-6-en-3-ol with 145 mg (0.51 mmol) of dimethyl 4-bromomethylphthalate, 131 mg (74%) of expected product are obtained in the form of an oil.

Sources & evidence

ORD record
ord-20ea0a9ee06d4a6bb2c8bb1b96f15a02
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

Loading…