Malonic Acid → (2E)-3-(2-Fluoro-5-methoxyphenyl)prop-2-enoic acid

HRID 1822963Notes

Reaction equation

HRID 1822963 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>N1C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1/[CH:4]=[CH:13]/[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 22171186(2E)-3-(2-Fluoro-5-methoxyphenyl)prop-2-enoic acidYield 95.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-fluoro-5-methoxybenzaldehyde (10.00 g, 64.9 mmol), malonic acid (13.4 g, 128.8 mmol), piperidine (2.00 mL) and pyridine (100 mL) was heated to 110° C. for 2 h. After this time the solvent was removed in vacuo and the residue taken up in ethyl acetate and washed with aqueous hydrochloric acid (2N, 100 mL). The organic solvent was dried (MgSO4) and the solvent evaporated in vacuo. The solid was recrystallised from hot etahanol to give a white solid (12.2 g, 95%); δH (300 MHz, DMSO) 7.60 (1H, d, J 7 Hz, CH═C), 7.31–7.28 (1H, m, Ar), 7.20 (1H, t, Ar), 7.07–6.97 (1H, m, Ar), 6.62 (1H, d, J 8 Hz, CH═CH), 3.80 (3H, s, OCH3).

Workup

  1. customAfter this time the solvent was removed in vacuo
  2. washwashed with aqueous hydrochloric acid (2N, 100 mL)
  3. dry with materialThe organic solvent was dried (MgSO4)
  4. customthe solvent evaporated in vacuo
  5. customThe solid was recrystallised from hot etahanol

Sources & evidence

ORD record
ord-44b2a812db164ef88852c3955cf9bc61
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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