Hydrochloric Acid → 2,3-Dichloro-4-methoxycinnamic acid

HRID 1157039Notes

Reaction equation

HRID 1157039 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 130156892,3-Dichloro-4-methoxybenzaldehyde

Product 1

HCID 536752552,3-Dichloro-4-methoxycinnamic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2,3-dichloro-4-methoxybenzaldehyde (158 gm., 0.77 mole), malonic acid (146 gm., 1.4 mole), pyridine (450 ml.) and piperidine (15 ml.) is heated and stirred on a steam bath for 23/4 hours. The hot reaction mixture is poured, with stirring into a mixture of concentrated hydrochloric acid (770 ml.) and crushed ice (3.1 kg.).

Workup

  1. temperatureis heated
  2. additionThe hot reaction mixture is poured

Sources & evidence

ORD record
ord-fb12a027fe1447e98c15360e385a850a
Source dataset
uspto-grants-1982_06
Patent number
US04337354

Reaction notes

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