Hydrochloric Acid → p-Bromocinnamic acid

HRID 2068589Notes

Reaction equation

HRID 2068589 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1.Cl>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:11][C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 707414-Bromobenzaldehyde

Product 1

HCID 99777p-Bromocinnamic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 4-bromobenzaldehyde, 1 (110 g, 0.59 mol), malonic acid (112.5 g, 1.189 mol), piperidine (11 mL) in pyridine (350 mL) was heated to 80° C. for 1 h, then refluxed for 3 h. Then the reaction mixture was cooled to room temperature, poured into a large beaker filled with cold water, and then acidified (pH<3) by slowly adding 25 mL of concentrated hydrochloric acid. The resulting precipitate was filtered and washed with cold water. The crude product was dissolved in aqueous sodium hydroxide, acidified (pH<3) (1:1 hydrochloric acid/water), filtered, and washed (cold water). The solid was dried in vacuo (60-70° C.) to give 2 (118.8 g, 88%).

Workup

  1. temperaturerefluxed for 3 h
  2. additionpoured into a large beaker
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with cold water
  5. dissolutionThe crude product was dissolved in aqueous sodium hydroxide
  6. filtrationfiltered
  7. washwashed (cold water)
  8. customThe solid was dried in vacuo (60-70° C.)

Sources & evidence

ORD record
ord-d6521f0e775e46368be0cf9193846298
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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