Acrylic Acid → Oxan-2-yl prop-2-enoate

HRID 1585452Notes

Reaction equation

HRID 1585452 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1>ClCCl>[C:1]([O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)(=[O:4])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 21909470Oxan-2-yl prop-2-enoateYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr.

Workup

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate
  2. concentrationthe organic layer was concentrated in vacuo
  3. distillationThe residue was distilled

Sources & evidence

ORD record
ord-f8c2f1945ec4400a87e4fce8bec28ec1
Source dataset
uspto-grants-1999_08
Patent number
US05939237

Reaction notes

Loading…