Triethylamine → 2-Methyl acrylic acid 3-(4'-propyl-bicyclohexyl-4-yl)-propyl ester

HRID 386330Notes

Reaction equation

HRID 386330 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][OH:19])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C(N(CC)CC)C.[C:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29]>ClCCl>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][O:19][C:27](=[O:31])[C:28]([CH3:30])=[CH2:29])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 184179123-(trans-4-(trans-4-Propylcyclohexyl)cyclohexyl)propanol

Product 1

HCID 592890482-Methyl acrylic acid 3-(4'-propyl-bicyclohexyl-4-yl)-propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(4′-Propyl-bicyclohexyl-4-yl)-propan-1-ol (5 g, 18.8 mmol) is dissolved in dichloromethane (50 ml) and triethylamine (3.5 ml) and a solution of methacryloyl chloride (2.2 ml, 21.8 mmol) in dichloromethane (30 ml) is added dropwise at 0° C. The reaction is stirred overnight, evaporated, filtered through silica with heptane/ethyl acetate (19:1) and the crude product is crystallised from ethanol to give 2-methyl acrylic acid 3-(4′-propyl-bicyclohexyl-4-yl)-propyl ester as colourless crystals.

Workup

  1. customevaporated
  2. filtrationfiltered through silica with heptane/ethyl acetate (19:1)
  3. customthe crude product is crystallised from ethanol

Sources & evidence

ORD record
ord-e73418a263144a799439ebd5c9069d62
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

Loading…