Nitric Acid → 2-Butene, 3-methyl-1,1-bis[(3-methyl-2-butenyl)oxy]-

HRID 2163310Notes

Reaction equation

HRID 2163310 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH:4]=[O:5].[CH3:7][C:8]([CH3:12])=[CH:9][CH2:10][OH:11].[N+]([O-])(O)=O>O>[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][O:5][CH:10]([O:11][CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])[CH:9]=[C:8]([CH3:12])[CH3:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 111733-Methyl-2-buten-1-OLHCID 610203-Methyl-2-butenal

Product 1

HCID 98995152-Butene, 3-methyl-1,1-bis[(3-methyl-2-butenyl)oxy]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

690 g (8.2 moles) of 3-methyl-but-2-en-1-al, 1730 g (20 moles) of 3-methyl-but-2-en-1-ol and 23 mg of 65% strength nitric acid (corresponding to 0.62 × 10-4 % by weight of 100% strength HNO3, based on 2,420 g of starting compounds) are boiled under 60 mm Hg in a 4 liter flask surmounted by a packed column (filled with 5 mm Raschig rings). The bottom temperature assumes a value of 76-88° C. The packed column has a diameter of 45 mm and has 30 theoretical plates. The water formed in the reaction is taken off at the top of the column and the organic material which separates from the water is returned continuously into the top of the column. With a reflux of 600 g/hour, quantitative conversion of the aldehyde is achieved after 4.5 hours. 1,1-Bis-(3-methyl-but-2-en-1-yl-oxy)-3-methyl-but-2-ene is obtained about 99% pure after distilling off the excess alcohol, the yield being 98.6% based on 3-methyl-but-2-en-1-al and 98.2% based on 3-methyl-but-2-en-1-ol.

Workup

  1. additionsurmounted by a packed column (filled with 5 mm Raschig rings)
  2. customa value of 76-88° C

Sources & evidence

ORD record
ord-05bc60bf64ed481b94059d5940c515fa
Source dataset
uspto-grants-1979_01
Patent number
US04133836

Reaction notes

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