Propiovanillone → 4-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)-but-1-en-2-yl)-2-methoxyphenol

HRID 626126Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][C:3]=1[O:12][CH3:13].[Cl:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=O)=[CH:20][CH:19]=1>>[Cl:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:12][CH3:13])[CH:4]=2)[CH2:9][CH3:10])=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 15782Propiovanillone

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

Product 1

HCID 1239687854-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)-but-1-en-2-yl)-2-methoxyphenolYield 38.5%

Procedure

Following general procedure of McMurry reaction as example 1, step B described, 1-(4-hydroxy-3-methoxyphenyl)propan-1-one (207 mg, 1.15 mmol) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (318 mg, 1.15 mmol) to give 188 mg desired product (38.5% yield).

Workup

customgeneral procedure of McMurry reaction as example 1, step B

Sources & evidence

ORD record: ord-b4a9a8c3262f4672bae4d88ea5bf01c1
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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