Benzenepropanoic acid → 3-[4-(Chloroacetyl)phenyl]propionic acid

HRID 2419368Notes

Reaction equation

HRID 2419368 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][CH2:13][C:14](Cl)=[O:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)CCl>[Cl:12][CH2:13][C:14]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:2][CH:3]=1)=[O:15]

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 203155713-[4-(Chloroacetyl)phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 3-phenylpropionic acid (50g.) in ethylenedichloride (200ml.) was added over 1 hour to a stirred mixture of chloroacetyl chloride (37.7g.) and aluminum chloride (48.9g.) in ethylene dichloride (550ml.) at room temperature. The resulting mixture was stirred for 1 hour and was then poured cautiously onto a mixture of ice (2kg.) and concentrated hydrochloric acid (50ml.). After stirring for a further 16 hours, the crude product was separated by filtration and recrystallised from water to give 3-[4-(chloroacetyl)phenyl]propionic acid, m.p. 151°-153° C.

Workup

  1. stirringAfter stirring for a further 16 hours
  2. customthe crude product was separated by filtration
  3. customrecrystallised from water

Sources & evidence

ORD record
ord-8f7c1a316680455da42061af6cb0f46d
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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