3-Methoxybenzaldehyde → 3-methoxy-beta-methylstyrene Oxide

HRID 1155856Notes

Reaction equation

HRID 1155856 reaction equation
[C:1]1([SH+]C2C=CC=CC=2)C=CC=C[CH:2]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20]>O1CCCC1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]1[O:20][CH:1]1[CH3:2]

Participants

4

Reactant 2

HCID 115693-MethoxybenzaldehydeHCID 22290449Diphenylsulfonium

Product 1

HCID 204969033-methoxy-beta-methylstyrene Oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a -78° C. solution of diphenylsulfonium ethylide (1.0 mole) in tetrahydrofuran (one liter) is slowly added 3-methoxybenzaldehyde (1.0 mole). The reaction mixture is stirred at -78° C. for 3 hours and then allowed to warm to room temperature. It is then added to ether-water and the ether phase separated. The ether phase is washed with water, dried (MgSO4) and evaporated. Fractional distillation of the residue gives the title product.

Workup

  1. customTo a -78° C.
  2. temperatureto warm to room temperature
  3. customthe ether phase separated
  4. washThe ether phase is washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-df93ce4c427b4aaa953b7203d25ad902
Source dataset
uspto-grants-1982_06
Patent number
US04332942

Reaction notes

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