3,5-Dimethoxybenzaldehyde → 3,5-Dimethoxy-beta-methylstyrene oxide

HRID 1702178Notes

Reaction equation

HRID 1702178 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]=[C:22]([O:24][CH3:25])[CH:23]=1)[CH:19]=[O:20]>O1CCCC1>[CH3:25][O:24][C:22]1[CH:21]=[C:18]([CH:17]=[C:16]([O:15][CH3:14])[CH:23]=1)[CH:19]1[O:20][CH:1]1[CH3:2]

Participants

4

Reactant 2

HCID 817473,5-DimethoxybenzaldehydeHCID 22290449Diphenylsulfonium

Product 1

HCID 130604403,5-Dimethoxy-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 3,5-dimethoxybenzaldehyde (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-f6fabb00e5e945168cf82a8f5610b1a3
Source dataset
uspto-grants-1983_04
Patent number
US04380542

Reaction notes

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