Malonic Acid → 3-(3-Bromo-4-methoxyphenyl)-2-propenoic acid

HRID 1746839Notes

Reaction equation

HRID 1746839 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:13][C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 986623-Bromo-4-methoxybenzaldehyde

Product 1

HCID 7197543-(3-Bromo-4-methoxyphenyl)-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Bromo-4-methoxybenzaldehyde (50 g, 232 mmol), malonic acid (36.3 g, 348 mmol) and 250 ml of anhydrous pyridine are introduced into a 500 ml round-bottomed flask. Piperidine (11.4 ml, 116 mmol) is added and the medium is brought to reflux for 3 h. The pyridine is removed under vacuum and the medium is run on to 500 ml of a 1M aqueous hydrochloric acid solution. The solid is filtered off, washed with water and dried over P2O5.

Workup

  1. temperatureto reflux for 3 h
  2. customThe pyridine is removed under vacuum
  3. filtrationThe solid is filtered off
  4. washwashed with water
  5. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-5cd5ab68cf6e457b9ebfa83f299202cc
Source dataset
uspto-grants-2015_10
Patent number
US09150544B2

Reaction notes

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