p-Anisoyl chloride → 4-methacryloyloxybutyl (E)-3-[4-(4-methoxyphenylcarbonyloxy)phenyl]acrylate

HRID 1735923Notes

Reaction equation

HRID 1735923 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29](=[O:33])[C:30]([CH3:32])=[CH2:31])=[O:22])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29](=[O:33])[C:30]([CH3:32])=[CH2:31])=[O:22])=[CH:15][CH:14]=2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 220777254-methacryloyloxybutyl (E)-3-(4-hydroxyphenyl)acrylate

Product 1

HCID 675704504-methacryloyloxybutyl (E)-3-[4-(4-methoxyphenylcarbonyloxy)phenyl]acrylateYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.0 g of 4-methoxybenzoyl chloride in 25 ml of dichlormethane were added dropwise at 0° C. while stirring within 30 min. to a solution of 3.5 g of 4-methacryloyloxybutyl (E)-3-(4-hydroxyphenyl)acrylate and 1.2 g of triethylamine in 40 ml of dichloromethane. The reaction mixture was stirred at room temperature overnight, then filtered and subsequently concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 7:3) and two-fold recrystallization from ethanol gave 4.5 g of 4-methacryloyloxybutyl (E)-3-[4-(4-methoxyphenylcarbonyloxy)phenyl]acrylate, m.p. 89°-90° C.

Workup

  1. filtrationfiltered
  2. concentrationsubsequently concentrated
  3. customChromatographic purification of the residue on silica gel
  4. customwith hexane/ethyl acetate (vol. 7:3) and two-fold recrystallization from ethanol

Sources & evidence

ORD record
ord-aa56edd608ce46dba02aba381392694e
Source dataset
uspto-grants-1996_07
Patent number
US05539074

Reaction notes

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