Toluene → Benzenepropanoyl chloride

HRID 1198392Notes

Reaction equation

HRID 1198392 reaction equation
C1([CH:7](C)[C:8]([OH:10])=O)C=CC=CC=1.S(Cl)([Cl:14])=O.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:16]1([CH2:22][CH2:7][C:8]([Cl:14])=[O:10])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 102962-Phenylpropionic acidHCID 24386Thionyl Chloride

Product 1

HCID 64801Benzenepropanoyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred suspension of phenylpropionic acid (120 g) in toluene (120 ml) and pyridine (6 ml) was added thionyl chloride (115 ml), vigorous gassing ensued and the temperature fell rapidly to 5° C. Reaction was complete in 1 h and the solvent was evaporated in vacuo. The residue was redissolved in toluene (120 ml), the solution was filtered to remove pyridine hydrochloride and the filtrate was evaporated in vacuo to give 166 g of phenylpropionyl chloride.

Workup

  1. customfell rapidly to 5° C
  2. customReaction
  3. customthe solvent was evaporated in vacuo
  4. dissolutionThe residue was redissolved in toluene (120 ml)
  5. filtrationthe solution was filtered
  6. customto remove pyridine hydrochloride
  7. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-eee8d936525749d2917cb850cb77a942
Source dataset
uspto-grants-1994_01
Patent number
US05281598

Reaction notes

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