Methanol → 1-(Cyclohexylidene(4-methoxyphenyl)methyl)-4-methoxybenzene

HRID 1608883Notes

Reaction equation

HRID 1608883 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH:10]1([C:16](OC)=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH3:20][OH:21]>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]([C:10]2[CH:11]=[CH:12][C:13]([O:21][CH3:20])=[CH:14][CH:15]=2)=[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 77304-BromoanisoleHCID 20748Methyl cyclohexanecarboxylate2×

Product 1

HCID 824581-(Cyclohexylidene(4-methoxyphenyl)methyl)-4-methoxybenzene

Procedure

The Grignard reaction of p-bromoanisole (15.0 g, 0.080 mol) and methyl cyclohexane carboxylate (Compound 26) (5.7 g, 0.040 mol) afforded the carbinol (Compound 27) which upon dehydration yielded a yellow solid. Recrystallized from absolute EtOH yielded 8.0 g (65%) of a colorless solid, mp 106°-107° C. (MIQUEL, J -F., WAHLSTAM, H., OLSSON, K. AND SUNDBECK, B. (1963), "Synthesis of unsymmetrical diphenylalkenes", Journal of Medicinal Chemistry, 6, 774), 109°-110° C. 1H NMR (CDCl3) δ 1.70 (broad s, 10H, cyclohexyl), 3.70 (s, 6H, OCH3), 7.07 (dd, 8H, ArH).

Workup

  1. customyielded a yellow solid
  2. customRecrystallized from absolute EtOH
  3. customyielded

Sources & evidence

ORD record
ord-e194a98366e84cecbd2913f84873bb12
Source dataset
uspto-grants-1995_03
Patent number
US05397802

Reaction notes

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