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

HRID 614129

Reaction equation

HRID 614129 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-fa804b3edd3946e889413e5d1127e934
Source dataset
uspto-grants-1979_03
Patent number
US04143139

Linked notes

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