Formaldehyde → Dimethyl alpha-hydroxymethyl-alpha-fluoromalonate

HRID 1614782Notes

Reaction equation

[F:1][CH:2]([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4].[CH2:11]=[O:12]>>[OH:12][CH2:11][C:2]([F:1])([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

Reactant 2

HCID 712Formaldehyde

HCID 2737111Dimethyl fluoromalonate

Product 1

HCID 10910147Dimethyl alpha-hydroxymethyl-alpha-fluoromalonate

Procedure

The process according to the invention for preparing an α-fluoroacrylic acid ester is carried out in three stages. First dimethyl α-fluoromalonate is reacted with formaldehyde to give dimethyl α-hydroxymethyl-α-fluoromalonate, which is then hydrolyzed and the hydrolysis product is dicarboxylated and dehydrated, and finally the resulting α-fluoroacrylic acid is esterified with an alcohol of the formula (3).

Sources & evidence

ORD record: ord-14f203eec57d41cebc734e72530bd0e7
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05198925

Reaction notes

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