Potassium Carbonate → HCID 178491285, compound

HRID 1689775Notes

Reaction equation

HRID 1689775 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:14][C:11]2[CH:10]=[CH:9][C:8]([C@H:5]3[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]3)=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 178516056HCID 178516056, compound

Product 1

HCID 178491285HCID 178491285, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of p-(trans-4-hydroxycyclohexyl)phenol (67.62 mmol, 13.00 g) in acetone (400 mL) is added 1-bromomethyl-4-methoxybenzene (74.38 mmol, 10.57 mL) and potassium carbonate (81.14 mmol, 11.33 g). The mixture is stirred for 64 h at room temperature and filtered. The filtrate is concentrated and recrystallized from CH2Cl2 (100 mL) to give the title compound (15.1 g, 71%) as a white solid. 1H NMR (400 MHz, CDCl3): 1.34-1.49 (m, 4H), 1.87-1.90 (m, 2H), 2.02-2.07 (m, 2H), 2.38-2.45 (m, 1H), 3.61-3.68 (m, 1H), 3.79 (s, 3H), 4.93 (s, 2H), 6.88 (d, 2H, J=8.8 Hz), 6.89 (d, 2H, J=8.8 Hz), 7.09 (d, 2H, J=8.8 Hz), 7.32 (d, 2H, J=8.8 Hz).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated
  3. customrecrystallized from CH2Cl2 (100 mL)

Sources & evidence

ORD record
ord-869850295bc1478ba187c10d998d9eed
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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