Isobutyraldehyde → Benzene, [(2-methyl-1-propenyl)thio]-

HRID 2049830Notes

Reaction equation

HRID 2049830 reaction equation
[C:1]1([S:7][CH2:8][Si](C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([Li])[CH2:14][CH2:15]C.CC(C)C=O>C1COCC1.CCCCCC.[Cl-].[Na+].O>[C:1]1([S:7][CH:8]=[C:14]([CH3:15])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 6561IsobutyraldehydeHCID 140295Silane, trimethyl((phenylthio)methyl)-HCID 178418339Butyllithium

Product 1

HCID 12308536Benzene, [(2-methyl-1-propenyl)thio]-

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3.92 g (20 mmol) of phenylthiomethyltrimethylsilane in 10 ml THF at 0° is added 20 ml n-butyllithium in hexane. The resulting yellow solution is stirred for 15 min at 0°, and a solution of 1.44 g (20 mmol) of 2-methyl-1-propanal in 5 ml THF is added. The reaction mixture is stirred for 15 min at 0°, then for 2 hr at 25°. Brine (15 ml) is added and the product extracted with ether. The organic layer is dried over calcium sulfate, filtered and the solvent is removed under vacuum to give 2-methyl-1-propenyl phenyl sulfide, which is purified by distillation under vacuum.

Workup

  1. stirringThe reaction mixture is stirred for 15 min at 0°
  2. waitfor 2 hr at 25°
  3. extractionthe product extracted with ether
  4. dry with materialThe organic layer is dried over calcium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-a31de550f0124297ae48d5445b3a20b4
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

Loading…