Methyl iodide → 2-(5-Methoxy-2-methylphenyl)-[1,3]dioxolane

HRID 322981Notes

Reaction equation

HRID 322981 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[O:14][CH2:13][CH2:12][O:11]1.[CH2:15]([Li])CCC.CI>O1CCCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:15])=[C:3]([CH:10]2[O:14][CH2:13][CH2:12][O:11]2)[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 111845031,3-Dioxolane, 2-(2-bromo-5-methoxyphenyl)-HCID 178418339Butyllithium

Product 1

HCID 221712332-(5-Methoxy-2-methylphenyl)-[1,3]dioxolane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

A stirred solution of 2-(2-bromo-5-methoxyphenyl)-[1,3]dioxolane (25.92 g) in tetrahydrofuran (400 mL) at −70° C. is treated dropwise with a solution of n-butyl lithium in hexanes (48.0 mL, 2.5 M). After stirring for 10 minutes methyl iodide (21.29 g) is added dropwise whilst maintaining the temperature at −65° C. The reaction mixture is stirred at −65° C. for 1 hour, allowed to warm to room temperature and stirring is continued for a further hour. The reaction mixture is evaporated and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase is washed with brine (500 mL),dried over magnesium sulphate and evaporated to give 2-(5-methoxy-2-methyl-phenyl)-[1,3]dioxolane (18.25 g) as a yellow oil.

Workup

  1. additionis added dropwise
  2. temperatureto warm to room temperature
  3. stirringstirring
  4. waitis continued for a further hour
  5. customThe reaction mixture is evaporated
  6. customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
  7. washThe organic phase is washed with brine (500 mL),dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-82e3fcedf4dd42e0803a1b9eea3c4cc5
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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