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

HRID 1636796Notes

Reaction equation

HRID 1636796 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

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 treated at 100° C. for 3.5 hours. 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. additiontreated at 100° C. for 3.5 hours
  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-fb9565164f954c4c8f46be360100ea7c
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Reaction notes

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