Ethylene Glycol → 2-Cyclohexylbenzaldehyde

HRID 1073480Notes

Reaction equation

HRID 1073480 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 11095317HCID 11095317, compound

Product 1

HCID 145521102-CyclohexylbenzaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

16.3 g. (0.1 mol) o-(1-Cyclohexenyl)-benzaldehyde were heated for 4 hours in a Dean and Stark apparatus with 6.85 g. (0.11 mol) ethyleneglycol and 1 g. p-toluenesulphonic acid in 400 ml. toluene. Thereafter, the calculated amount of water had separated off. The isolated protected aldehyde was taken up in ethanol and hydrogenated over platinum oxide as catalyst. After filtering and evaporating off the solvent, the crude product was taken up in 300 ml. dioxan, mixed with 80 ml. of a 10% aqueous solution of oxalic acid and heated under reflux for 2 hours. After extraction with ethyl acetate, the organic phase was washed with water, dried over anhydrous magnesium sulphate and evaporated. Flash chromatography (hexane/ethyl acetate 5:1 v/v) gave the aldehyde in pure form in a yield of 65% of theory.

Workup

  1. customThereafter, the calculated amount of water had separated off
  2. filtrationAfter filtering
  3. customevaporating off the solvent
  4. additiondioxan, mixed with 80 ml
  5. temperatureof a 10% aqueous solution of oxalic acid and heated
  6. temperatureunder reflux for 2 hours
  7. extractionAfter extraction with ethyl acetate
  8. washthe organic phase was washed with water
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-55bc59bfedd84bb3a82af1318b5d27b4
Source dataset
uspto-grants-1990_11
Patent number
US04970077

Reaction notes

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