Carbon Disulfide → Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

HRID 557875Notes

Reaction equation

HRID 557875 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].C(=S)=S>Cl>[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 6348Carbon DisulfideHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Aluminum trichloride (7.9 g, 0.060 mol) was added in portions to a mixture of methyl 1-phenylcyclopropanecarboxylate (3.5 g, 0.020 mol) and chloroacetyl chloride (2.0 mL, 0.026 mol) in carbon disulfide (40 mL, 0.7 mol) at 15-25° C. and then the reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into conc. HCl (10 mL) in ice (100 g) and then extracted with ether. The ether extract was washed with brine, dried and concentrated. The product was purified by CombiFlash using hexane/EtOAc (max.EA 20%). The final product was analyzed by 1H NMR, which showed that the product was a mixture of para and meta substituted isomers with a ratio of 3:2.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe product was purified by CombiFlash
  7. additiona mixture of para and meta

Sources & evidence

ORD record
ord-fd0721828f264eb8a5467b8f5dbea1b5
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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