Hydrochloric Acid → 3-(2-Benzyloxy-5-bromophenyl)-acrylic acid

HRID 50591

Reaction equation

HRID 50591 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1.Cl>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=[CH:19][C:20]([OH:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 7330872-(Benzyloxy)-5-bromobenzaldehyde

Product 1

HCID 46633083-(2-Benzyloxy-5-bromophenyl)-acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-benzyloxy-5-bromobenzaldehyde (0.10 mol), malonic acid (15.0 g), and piperidine (2.0 ml) in 150 ml of pyridine was first heated at 90° C. for 90 min and subsequently refluxed for 0.5 hrs. After cooling to room temperature, the reaction was poured on a mixture of ice (1 kg) and concentrated aqueous hydrochloric acid (250 ml). The solid material that precipitated after stirring for 2 hrs. was collected by suction and recrystallized from a minimum of boiling methanol.

Workup

  1. temperaturesubsequently refluxed for 0.5 hrs
  2. temperatureAfter cooling to room temperature
  3. customThe solid material that precipitated
  4. customwas collected by suction
  5. customrecrystallized from a minimum of boiling methanol

Sources & evidence

ORD record
ord-73bc53d3447d4ac1b88413f2260d1dcb
Source dataset
uspto-grants-2004_03
Patent number
US06713464B1

Linked notes

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