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

HRID 1029349

Reaction equation

HRID 1029349 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-4e009b6f86f44acf8a27f606ca8b642b
Source dataset
uspto-grants-1992_04
Patent number
US05102771

Linked notes

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