Triethylamine → HCID 54303311, compound

HRID 2073647Notes

Reaction equation

HRID 2073647 reaction equation
Cl[C:2]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)=[O:3].BrC1C=CC(C(O)=[O:23])=CC=1.C(OCC)(=O)C=C.C(N(CC)CC)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:2]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)([OH:23])=[O:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 114644-Bromobenzoic acidHCID 54300281HCID 54300281, compound

Product 1

HCID 54303311HCID 54303311, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

The ethyl 4-chloroformylcinnamate can be prepared as follows: 10.05 g (50 mmols) of 4-bromobenzoic acid, 6.25 g (62.5 mmols) of ethyl acrylate, 12.6 g (125 mmols) of triethylamine, 0.1122 g (0.5 mmol) of palladium acetate and 0.608 g (2 mmols) of tri-o-tolylphosphine in 20 ml of toluene are boiled under reflux for 1.5 hours. The reaction mixture is extracted by shaking with 200 ml of 2N hydrochloric acid, and the crude product is filtered off and recrystallised from toluene. 10.1 g (92% of theory) of ethyl 4-carboxycinnamate are obtained in the form of white crystals; melting point 196°-197° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. extractionThe reaction mixture is extracted
  3. filtrationthe crude product is filtered off
  4. customrecrystallised from toluene

Sources & evidence

ORD record
ord-bec24f6fe8ae44d0aad980ffcf4437fe
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

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