Malonic Acid → (2E)-3-(4-Fluoro-2-methoxyphenyl)-2-propenoic acid

HRID 1852112Notes

Reaction equation

HRID 1852112 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH3:11])[CH:3]=1.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>N1C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:13]/[C:14]([OH:16])=[O:15])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 27745374-Fluoro-2-methoxybenzaldehyde

Product 1

HCID 23150778(2E)-3-(4-Fluoro-2-methoxyphenyl)-2-propenoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-fluoro-2-methoxybenzaldehyde (1.0 g, 6.49 mmol) and malonic acid (1.350 g, 12.98 mmol) in pyridine (10 mL) was refluxed for 16 h. After concentration the residue was taken into water. The solid was filtered, washed with water, then dried to give (E)-3-(4-fluoro-2-methoxyphenyl)acrylic acid (1.22 g, 96% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.03 (d, J=16.1 Hz, 1H), 7.53 (dd, J=8.5, 6.8 Hz, 1H), 6.75-6.65 (m, 2H), 6.52 (d, J=16.1 Hz, 1H), 3.92 (s, 3H).

Workup

  1. concentrationAfter concentration the residue
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-779739d2c2ce4de2803183c9849c8f7d
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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