Hydrochloric Acid → Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

HRID 504308Notes

Reaction equation

HRID 504308 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]1([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].Cl>C(=S)=S>[Cl:18][CH2:19][C:20]([C:8]1[CH:9]=[CH:10][C:5]([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)=[CH:6][CH:7]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Product 1

HCID 86602275Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Aluminium trichloride (7.9 g, 60.0 mmol) was added in portions to a mixture of methyl 1-phenylcyclopropanecarboxylate (3.5 g, 20.0 mmol) and chloroacetyl chloride (2.0 mL, 26.0 mmol) in carbon disulfide (40.0 mL) at 15-25° C. The reaction mixture was stirred for 2 hours at room temperature. Then the mixture was poured into concentrated HCl (10.0 mL) in ice (100 g). The resulting mixture was extracted with diethyl ether several times. The combined organic phase was washed with brine, then dried and concentrated. The crude product was purified by CombiFlash using hexane/ethyl acetate.

Workup

  1. extractionThe resulting mixture was extracted with diethyl ether several times
  2. washThe combined organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by CombiFlash

Sources & evidence

ORD record
ord-51b58c56d52f4540919f1755af9bf14f
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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