Triethylamine → Methyl 2-(4-chlorophenyl)acrylate

HRID 79542

Reaction equation

HRID 79542 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13]O)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH2:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19914733Methyl 2-(4-chlorophenyl)-3-hydroxypropanoate

Product 1

HCID 11735736Methyl 2-(4-chlorophenyl)acrylateYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-(4-chlorophenyl)-3-hydroxypropanoate (16.2 g, 75.5 mmol) was dissolved in DCM (200 mL). Triethylamine (26.3 mL, 188.7 mmol) was then added, and the solution was cooled to 0° C. The solution was then treated with methanesulfonyl chloride (5.84 mL, 75.5 mmol), and the mixture was stirred at 0° C. for 30 minutes. The cold solution was acidified to a pH of 1, and extracted with methylene chloride. The combined organic layers were washed with 1N HCl, water, 6% NaHCO3, dried over Na2SO4 and concentrated. The crude oil was filter chromatographed on SiO2 (with gypsum, Aldrich 28,852-7, 350 g) and eluted with 20:1 hexane:EtOAc to give methyl 2-(4-chlorophenyl)acrylate (10.9 g, 73%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers were washed with 1N HCl, water, 6% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. filtrationThe crude oil was filter
  6. customchromatographed on SiO2 (with gypsum, Aldrich 28,852-7, 350 g)
  7. washeluted with 20:1 hexane

Sources & evidence

ORD record
ord-c552b8dec63e47c2bdd4cfee970a4e59
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Linked notes

Loading…