2-Ethylbutyraldehyde → 1,3-Dioxepin, 2-(1-ethylpropyl)-4,7-dihydro-

HRID 1606790Notes

Reaction equation

HRID 1606790 reaction equation
[CH2:1]([CH:3]([CH2:6][CH3:7])[CH:4]=[O:5])[CH3:2].[CH2:8](O)[CH:9]=[CH:10][CH2:11][OH:12].C1CCCCC1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:2][CH2:1][CH:3]([CH:4]1[O:12][CH2:11][CH:10]=[CH:9][CH2:8][O:5]1)[CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 73592-EthylbutyraldehydeHCID 80652-Butene-1,4-diolHCID 8078Cyclohexane

Product 1

HCID 1044721,3-Dioxepin, 2-(1-ethylpropyl)-4,7-dihydro-Yield 86%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

To a one liter flask equipped with heating jacket, agitator and condenser fitted with a Dean-Stark trap was charged 100 grams (1.0 mole), 2-ethyl-butanal, 97 grams(1.1 mole) 2-butene-1,4-diol, 80 grams cyclohexane and 0.2 grams p-toluenesulfonic acid monohydrate. The mixture was heated with vigorous agitation at reflux (84° - 99°C.) until water no longer continued to be distilled from the reaction mixture (1.2 hours). The reaction mixture was cooled to room temperature and the p-toluenesulfonic acid neutralized by washing with reaction mixture with a 5% aqueous solution of sodium hydroxide. The reaction mixture was then washed neutral with water and distilled to remove the cyclohexane. The oil was vacuum distilled to obtain 146 grams (86% of theoretical) of 4,7-dihydro-2-(3-pentyl)-1,3-dioxepin having a boiling point of 47°C. at a pressure of 1.0 millimeter of mercury, (refractive index, ND20 = 1.457). Analysis for carbonyl content of IR showed 0.0% carbonyl and VPC analysis showed the compound to have a purity of 100%.

Workup

  1. customTo a one liter flask equipped
  2. temperaturewith heating jacket, agitator and condenser
  3. customfitted with a Dean-Stark trap
  4. temperatureThe mixture was heated with vigorous agitation
  5. distillationto be distilled from the reaction mixture (1.2 hours)
  6. washby washing with reaction mixture with a 5% aqueous solution of sodium hydroxide
  7. washThe reaction mixture was then washed neutral with water
  8. distillationdistilled
  9. customto remove the cyclohexane
  10. distillationdistilled

Sources & evidence

ORD record
ord-3ba13667ea854af8b86648d273b1973b
Source dataset
uspto-grants-1976_04
Patent number
US03953614

Reaction notes

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