Methane, dichloromethoxy- → 4-(Cyclopropylmethyl)benzaldehyde

HRID 1741830Notes

Reaction equation

HRID 1741830 reaction equation
[CH:1]1([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[CH3:11][O:12]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:1]1([CH2:4][C:5]2[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 74274Benzylcyclopropane

Product 1

HCID 190108254-(Cyclopropylmethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of (cyclopropylmethyl)benzene (1.32 g) and dichloromethyl methyl ether (1.25 ml) in dichloromethane (20 ml) was added 1.0M solution of titanium(IV) chloride in dichloromethane (15 ml) at 0° C. under nitrogen atmosphere. The mixture was stirred at 0° C. for 10 minutes, then poured into ice water. The organic layer was separated and washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (9:1) to give 4-(cyclopropylmethyl)benzaldehyde (580 mg) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column
  6. washeluting with a mixture of hexane and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-712cbbe59da443f3891f340902639b4e
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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