1-(4-Hydroxycyclohexyl)propan-1-one → 4-(1-(4-(2-Chloroethoxy)phenyl)-2-(4-hydroxycyclohexyl)but-1-enyl)phenol

HRID 626110Notes

Reaction equation

HRID 626110 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8](=O)[CH2:9][CH3:10])[CH2:4][CH2:3]1.[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=O)=[CH:18][CH:17]=1>>[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:8]([CH:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:9][CH3:10])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 510398611-(4-Hydroxycyclohexyl)propan-1-oneHCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

Product 1

HCID 1232527154-(1-(4-(2-Chloroethoxy)phenyl)-2-(4-hydroxycyclohexyl)but-1-enyl)phenolYield 52%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-(4-hydroxycyclohexyl)propan-1-one (0.6 g, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (1.6 g, 1.5 eq) to give 0.8 g desired product (52% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.11-7.20 (m, 1H), 7.00-7.10 (m, 2H), 6.90-6.70 (m, 1H), 6.60-6.89 (m, 3H), 6.58 (d, J=7.6 Hz, 1H), 4.08-4.20 (m, 2H), 3.70-3.80 (m, 2H), 3.60 (brs, 1H), 2.47 (q, J=7.6 Hz, 2H), 2.28-2.38 (m, 1H), 2.00-2.08 (m, 2H), 1.86-1.94 (m, 2H), 1.72-1.80 (m, 1H), 1.20-1.49 (m, 4H), 1.04 (t, J=7.6 Hz, 3H)

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-59cb78ec4a0e43bfa2bee931629c8b5c
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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