Malonic Acid → 3,5-Dichlorocinnamic acid

HRID 890758Notes

Reaction equation

HRID 890758 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>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:12][C:13]([OH:15])=[O:14])[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 357463,5-Dichlorobenzaldehyde

Product 1

HCID 1765043,5-Dichlorocinnamic acidYield 61.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3,5-dichlorobenzaldehyde (15.0 g, 85.7 mmol), malonic acid (12.5 g, 120.2 mmol), and piperidine (5 mL) was heated at 100° C. for 2 h and at 150° C. for 1 h. The reaction was poured onto 3N HCl (200 mL) and the precipitate was removed via filtration. The product was purified by recrystallization (100 mL hot EtOH) to afford 3-(3,5-dichlorophenyl)-acrylic acid (11.5 g). 1H NMR (250 MHz, DMSO-d6) δ 12.6 (bs, 1H), 7.83 (m, 2H), 7.64–7.51 (m, 2H), 6.72 (d, 1H).

Workup

  1. customthe precipitate was removed via filtration
  2. customThe product was purified by recrystallization (100 mL hot EtOH)

Sources & evidence

ORD record
ord-f5380f8d256d435a94ead8ce97fb2874
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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