Malonic Acid → HCID 58387360, compound

HRID 1184546Notes

Reaction equation

HRID 1184546 reaction equation
[F:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>N1C=CC=CC=1.N1CCCCC1>[F:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:13]/[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 5939092,4-Difluoro-3-hydroxybenzaldehyde

Product 1

HCID 58387360HCID 58387360, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Procedure

A mixture of 2,4-difluoro-3-hydroxybenzaldehyde (0.255 g, 1.613 mmol) and malonic acid (0.168 g, 1.613 mmol) in pyridine (6 ml) and piperidine (0.06 ml) was heated to reflux for 1 h. All the volatile were removed and the residue was partitioned between NaHCO3 sat. and Et2O. The aqueous phase was acidified with 37% HCl until pH<3 and extracted with AcOEt. The organic layer was dried over sodium sulphate and evaporated to give (E)-3-(2,4-difluoro-3-hydroxyphenyl)acrylic acid (280 mg) as pale a brown solid. The compound was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. customAll the volatile were removed
  4. customthe residue was partitioned between NaHCO3 sat. and Et2O
  5. extractionextracted with AcOEt
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-23be35ff430541288be5fd38e4c250b3
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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