Hydrochloric Acid → 3-(4-Fluoro-3-methoxyphenyl)prop-2-enoic acid

HRID 1593041Notes

Reaction equation

HRID 1593041 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1.Cl>N1C=CC=CC=1.O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:13][C:14]([OH:16])=[O:15])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 534043133-(4-Fluoro-3-methoxyphenyl)prop-2-enoic acidYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-fluoro-3-methoxybenzaldehyde (32 g, 0.2 mol) in pyridine (100 mL) was added malonic acid (43 g, 0.4 mol) and piperidine (3 mL, 0.03 mol). The reaction solution was stirred at 85° C. for 13 hr. Upon cooling, the resulting suspension was added to cold water (500 mL) and acidified with conc. HCl (80 mL). The white solid was filtered off, washed with water and dried to yield 36 g (92%) of 3-(4-fluoro-3-methoxyphenyl)-acrylic acid. RP-HPLC: 3.71 min. 1H-NMR (DMSO-d6) δ (ppm) 3.85 (s, 3), 6.53 (d, 1, J=16), 7.20 (m, 2), 7.50 (m, 1), 7.52 (d, 1, J=16).

Workup

  1. temperatureUpon cooling
  2. filtrationThe white solid was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3550d209127949a786385d4af8f367cb
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

Loading…