Triethylamine → 2-Methyl-acrylic acid 6-[4-(2-methoxycarbonyl-vinyl)-phenoxy]-hexyl ester

HRID 896723Notes

Reaction equation

HRID 896723 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30]>ClCCl>[CH3:1][O:2][C:3]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:28](=[O:32])[C:29]([CH3:31])=[CH2:30])=[CH:8][CH:7]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 67322893Methyl 3-{4-[(6-hydroxyhexyl)oxy]phenyl}prop-2-enoate

Product 1

HCID 673221982-Methyl-acrylic acid 6-[4-(2-methoxycarbonyl-vinyl)-phenoxy]-hexyl esterYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice-cooled solution of 20 g (72 mmol) 3-[4-(6-hydroxy-hexyloxy)-phenyl]-acrylic acid methyl ester, 11.7 g (116 mmol) triethylamine and 4 crystals of BHT in 150 ml of dichloromethane was added dropwise 11.3 g (108 mmol) of methacryloyl chloride in 5 ml dichloromethane. The mixture was allowed to react for 2 hours, at which time the dichloromethane was removed under reduced pressure. The mixture was partitioned between water (100 ml) and ethyl acetate (100 ml) and the aqueous layer subsequently extracted twice more with 100 ml portions of ethyl acetate. The combined organic layers were washed with 100 ml portions of 1M HCl, water, 5% sodium hydrogen carbonate and brine and then dried with magnesium sulfate and concentrated. Recrystallization from ethanol gave 18 g (72% yield) of a white solid.

Workup

  1. customwas removed under reduced pressure
  2. customThe mixture was partitioned between water (100 ml) and ethyl acetate (100 ml)
  3. extractionthe aqueous layer subsequently extracted twice more with 100 ml portions of ethyl acetate
  4. washThe combined organic layers were washed with 100 ml portions of 1M HCl, water, 5% sodium hydrogen carbonate and brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-69a9c7914b2f4427a68f53c2fdf815d6
Source dataset
uspto-grants-2005_07
Patent number
US06919404B2

Reaction notes

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