Malonic Acid → HCID 58387283, compound

HRID 1184544Notes

Reaction equation

HRID 1184544 reaction equation
[Cl:1][C:2]1[C:9]([OH: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>N1C=CC=CC=1.Cl>[Cl:1][C:2]1[C:9]([OH: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 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 603956Chloroisovaniline

Product 1

HCID 58387283HCID 58387283, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-3-hydroxy-4-methoxybenzaldehyde (1.86 g, 10 mmol) was dissolved in pyridine (7 ml), malonic acid (1.25 g, 10 mmol) and piperidine (0.1 ml) were added and the mixture was heated at 100° C. for 2 hrs, then it was poured in 100 ml HCl 1N and extracted with AcOEt. This was dried and evaporated, and the residue was triturated with diethyl ether and filtered, giving 2.10 g of (E)-3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-acrylic acid as a white solid, which was used without further purification.

Workup

  1. extractionextracted with AcOEt
  2. customThis was dried
  3. customevaporated
  4. customthe residue was triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c67fa988329049d5b5734d8acd17e20b
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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