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

HRID 1034127Notes

Reaction equation

HRID 1034127 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-1a9b6edd26bf4948b0ccb01a50c9bf06
Source dataset
uspto-grants-1994_05
Patent number
US05314785

Reaction notes

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