Malonic Acid → 3,5-Dichlorocinnamic acid

HRID 981579Notes

Reaction equation

HRID 981579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[CH:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 357463,5-Dichlorobenzaldehyde

Product 1

HCID 1765043,5-Dichlorocinnamic acidYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Reaction of 3,5-dichlorobenzaldehyde (26.9 g, 0.154 mole), malonic acid (24.1 g, 0.232 mole), pyridine (8 ml) and piperidine (0.4 ml) substantially as above yielded 22.9 g (69%) of 3,5-dichlorocinnamic acid as white needles: mp 169-170° (ethanol).

Sources & evidence

ORD record
ord-282a6ad4e33d492eb9305ceb564bdb6d
Source dataset
uspto-grants-1991_02
Patent number
US04992459

Reaction notes

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