Toluene → 2-Undecyl-4-hydroxymethyl-1,3-dioxolane

HRID 381723Notes

Reaction equation

HRID 381723 reaction equation
[CH:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:14]1([CH3:20])C=CC=C[CH:15]=1.C1(C)C=CC(S(O)(=O)=[O:28])=CC=1.[OH-:32].[Na+]>C(O)C>[CH2:2]([CH:1]1[O:13][CH:14]([CH2:15][OH:28])[CH2:20][O:32]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 8194DodecanalHCID 14798Sodium Hydroxide

Product 1

HCID 183640352-Undecyl-4-hydroxymethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Then, the same reactor as above was charged with 226 g of acetyl-1,2-isopropylideneglycerol, 221 g of n-dodecanal and a solvent amount of toluene. Thereafter, p-toluenesulfonic acid was added as a catalyst and the acetal exchange reaction was carried out under reflux conditions. Then, a solution of sodium hydroxide in ethanol was added to decompose the ester moiety at the reflux temperature and the ethanol was distilled off under reduced pressure. The resulting crude product was extracted into diethyl ether and washed with 3 portions of distilled water. The diethyl ether layer was dehydrated over potassium carbonate and the diethyl ether was distilled off under reduced pressure. The residue was further purified by distillation under reduced pressure to provide 2-undecyl-4-hydroxymethyl-1,3-dioxolane.

Workup

  1. distillationthe ethanol was distilled off under reduced pressure
  2. extractionThe resulting crude product was extracted into diethyl ether
  3. washwashed with 3 portions of distilled water
  4. distillationthe diethyl ether was distilled off under reduced pressure
  5. distillationThe residue was further purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-17f8444da464479bab81057845632566
Source dataset
uspto-grants-2001_10
Patent number
US06307069B1

Reaction notes

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