Water → Methyl 1-(4-chloromethylphenyl)cyclopropanecarboxylate

HRID 1282097Notes

Reaction equation

HRID 1282097 reaction equation
[C:1]1([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH2:16][Cl:17].O.CCCCCC>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:17][CH2:16][C:4]1[CH:5]=[CH:6][C:1]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)=[CH:2][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 8058HexaneHCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Product 1

HCID 18423090Methyl 1-(4-chloromethylphenyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-phenylcyclopropanecarboxylate (8.5 g) in methylene chloride (70 ml) was added titanium tetrachloride (8.0 ml) under ice-cooling. To this solution was added dropwise a solution of methoxymethyl chloride (5.5 ml) in methylene chloride (30 ml) under ice-cooling. The mixture was stirred at room temperature for 5 hr and left standing overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with an aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a pale-brown oil. The oil was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give the title compound (7.9 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitleft
  4. waitstanding overnight
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with an aqueous sodium hydrogencarbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customto give a pale-brown oil

Sources & evidence

ORD record
ord-b09844aaf2d947abba567a480a22d5c8
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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