2-Hydroxyethyl acrylate → 2-(Acryloyloxy)ethyl 5-carboxy-7-oxabicyclo [2.2.1]hept-2-ene-6-carboxylate

HRID 325440

Reaction equation

HRID 325440 reaction equation
[CH:1]12[O:12][CH:4]([CH:5]3[C:10](=[O:11])[O:9][C:7](=[O:8])[CH:6]31)[CH:3]=[CH:2]2.[C:13]([O:17][CH2:18][CH2:19][OH:20])(=[O:16])[CH:14]=[CH2:15]>C1(C)C=CC=CC=1>[C:10]([CH:5]1[CH:6]([C:7]([O:20][CH2:19][CH2:18][O:17][C:13](=[O:16])[CH:14]=[CH2:15])=[O:8])[CH:1]2[O:12][CH:4]1[CH:3]=[CH:2]2)([OH:9])=[O:11]

Participants

4

Reactant 2

HCID 131652-Hydroxyethyl acrylateHCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

Product 1

HCID 204648922-(Acryloyloxy)ethyl 5-carboxy-7-oxabicyclo [2.2.1]hept-2-ene-6-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Maleic anhydride (50 g) and furan (150 ml) were heated under reflux for 1 hour, and then the excess of furan was distilled off. The residue was recrystallised from chloroform, yielding 72 g of 7-oxabicyclo [2.2.1]hept-2-ene-5,6-dicarboxylic acid anhydride (m.pt. 110° C., decomp.). This anhydride (40 g) and 30.75 g of 2-hydroxyethyl acrylate were heated in 250 ml of toluene at 100° C. for 3 hours, and then the toluene was distilled off under reduced pressure, leaving the desired compound as a viscous liquid.

Workup

  1. distillationthe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9080267a457240da87884a2010723a7e
Source dataset
uspto-grants-1984_04
Patent number
US04440850

Linked notes

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