Hydrochloric Acid → 3-(3-Bromophenyl)acrylic acid

HRID 2778

Reaction equation

HRID 2778 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].Cl>N1CCCCC1.N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 765833-Bromobenzaldehyde

Product 1

HCID 362513-(3-Bromophenyl)acrylic acidYield 94.4%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromobenzaldehyde (10.0 g, 54 mmol), malonic acid (10.1 g, 97 mmol) and piperidine (0.267 mL, 2.7 mmol) are treated with pyridine (30 mL) and heated at 100° C. for 3.5 h. The reaction mixture is cooled to room temperature, poured into 200 ml of 20% hydrochloric acid at 0° C.; the resultant precipitate is collected, washed with copious amounts of water and dried in a vacuum dessicator overnight to afford the title compound (11.64 g, 51 mmol).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe resultant precipitate is collected
  3. washwashed with copious amounts of water
  4. customdried in a vacuum dessicator overnight

Sources & evidence

ORD record
ord-d723d805d22049e68439ec36653ca220
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

Loading…