Ethylene Oxide → 3-(2-Hydroxyethyl)butyrolactone

HRID 273906

Reaction equation

HRID 273906 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].[CH2:18]1[O:20][CH2:19]1>>[OH:6][CH2:7][CH2:8][CH:3]1[CH2:2][O:1][C:5](=[O:12])[CH2:4]1.[O:20]1[CH2:19][CH2:18][CH:10]([C:9]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:13]1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 8868Ethyl AcetoacetateHCID 2773573(Oxan-4-yl)methanol

Product 2

HCID 98773723-(2-Hydroxyethyl)butyrolactoneHCID 13467581Ethyl oxane-4-carboxylate

Procedure

It is known that 4-hydroxymethyltetrahydropyran can be prepared in three steps: reaction of ethyl acetoacetate with ethylene oxide to form 3-(2-hydroxyethyl)gamma-butyrolactone (EP-A-246 581), rearrangement to ethyl tetrahydropyran-4-carboxylate (EP-A-284 969), and subsequent catalytic hydrogenation to form 4-hydroxymethyltetrahydropyran (DE-A-4 141 222).

Workup

  1. customcan be prepared in three steps

Sources & evidence

ORD record
ord-482607a9bd004ff48a386bd144090d9e
Source dataset
uspto-grants-1995_02
Patent number
US05387701

Linked notes

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