Diethyl Malonate → Diethyl pentafluorobenzylmalonate

HRID 649249

Reaction equation

[F:1][C:2]1[C:7]([CH:8]=O)=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13].[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>>[F:1][C:2]1[C:7]([CH2:8][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13]

Participants

Reactant 2

HCID 7761Diethyl Malonate

HCID 69558Pentafluorobenzaldehyde

Product 1

HCID 88651511Diethyl pentafluorobenzylmalonateYield 69%

Procedure

9 g of pentafluorobenzaldehyde are condensed on 7 g of diethyl malonate in accordance with the process described in Organic Synthesis vol. III, page 377. 10 g (69%) of diethyl pentafluorobenzylmalonate are obtained which is hydrogenated at ordinary pressure in the presence of palladium on charcoal into diethyl pentafluorobenzylmalonate (92%).

Sources & evidence

ORD record: ord-16b1b55501134601a9cbffcc03de0787
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04738803

Linked notes

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