Methanol → HCID 53797537, compound

HRID 436532Notes

Reaction equation

HRID 436532 reaction equation
[CH3:1][C:2](=[CH:5][CH2:6][O:7][C:8](=[O:10])[CH3:9])[CH:3]=[O:4].CO.N1C2C(=CC=CC=2)C=C[CH:14]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:8]([O:7][CH:6]=[CH:5][C:2]([CH3:1])=[CH:3][O:4][CH3:14])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 7047QuinolineHCID 846993-Formylbut-2-enyl acetate

Product 1

HCID 53797537HCID 53797537, compoundYield 990.3%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

28.4 g (0.2 mole) of 2-methyl-4-acetoxy-2-butenal is dripped into a mixture of 23.3 g (0.22 mole) of o-formic acid methyl ester, 12.8 g (0.4 mole) of methanol and 0.35 g (2millimoles) of p-toluene-sulfonic acid. Acetalization takes place while the temperature rises. After 1 hour 2 g (15 millimoles) of quinoline is added and the whole is heated at 185° to 190° C (internal temperature) and at a pressure of 200 mm Hg for 20 minutes The methanol which is eliminated is distilled off in a 20-cm column. Then the pressure is adjusted to 20 mm Hg with the result that 23.2 g of 1-acetoxy-3-methyl-4-methoxy-1,3-butadiene in the form of a mixture of two geometric iosmers is obtained. The yield is 75% of the theory.

Workup

  1. temperaturethe whole is heated at 185° to 190° C (internal temperature)
  2. distillationat a pressure of 200 mm Hg for 20 minutes The methanol which is eliminated is distilled off in a 20-cm column

Sources & evidence

ORD record
ord-83699587fd2b4cc7a7b990f2486f4431
Source dataset
uspto-grants-1977_02
Patent number
US04009202

Reaction notes

Loading…