Allyl Alcohol → Methyl 2-(hydroxymethyl)prop-2-enoate

HRID 2402887Notes

Reaction equation

HRID 2402887 reaction equation
[OH:1][CH2:2][C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].N12CCN(CC1)CC2.[CH2:17](O)[CH:18]=[CH2:19]>>[CH2:19]([O:1][CH2:2][C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5])[CH:18]=[CH2:17].[OH:1][CH2:2][C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 9237DabcoHCID 11815329Methyl 2-(hydroxymethyl)prop-2-enoate2×

Product 2

HCID 11815329Methyl 2-(hydroxymethyl)prop-2-enoateHCID 24906004Methyl 2-((allyloxy)methyl)acrylate

Conditions

Temperature
95 °C

Procedure

A 100 mL 4-neck flask equipped with a stirrer, condenser, thermometer, gas inlet and oil bath was charged with 34.8 g of methyl α-(hydroxymethyl)acrylate, 3.4 g of 1,4-diazabicyclo[2.2.2]octane, and 0.02 g of 4-hydroxy-2,2,6,6-tetramethyl-1-oxyl as the polymerization inhibitor. Next, the temperature was raised to 95° C. and 26.2 g of allyl alcohol was added dropwise over 8 hours while stirring and blowing air into the reaction mixture, after which the reaction was continued for another 8 hours. Conversion of the methyl α-(hydroxymethyl)acrylate was 86 mol %, and the yields of methyl α(allyloxymethyl)acrylate and allyl ester with respect to the methyl α-(hydroxymethyl)acrylate were respectively 52.2 mol % and 1.0 mol %. The allyl ester content was 2.2 wt % per 100 wt % of methyl α-(allyloxymethyl)acrylate.

Workup

  1. customA 100 mL 4-neck flask equipped with a stirrer, condenser

Sources & evidence

ORD record
ord-3c91e30df0ee40a5a09c74af24cd6118
Source dataset
uspto-grants-2014_08
Patent number
US08796492B2

Reaction notes

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