Malonic Acid → 3,5-Dichlorocinnamic acid

HRID 2298159Notes

Reaction equation

HRID 2298159 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: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

4

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 357463,5-Dichlorobenzaldehyde

Product 1

HCID 1765043,5-Dichlorocinnamic acidYield 61.8%

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 HC1 (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. additionThe reaction was poured onto 3N
  2. custom(200 mL) and the precipitate was removed via filtration
  3. customThe product was purified by recrystallization (100 mL hot EtOH)

Sources & evidence

ORD record
ord-f68f53bbfb6b4cff87ad15a1eaf0dc1b
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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