1-Butanol → HCID 20329903, compound

HRID 971484Notes

Reaction equation

HRID 971484 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5]C(S(O)(=O)=O)=[CH:3][CH:2]=1.[O:12]([CH3:14])[Na].[CH2:15]([OH:19])[CH2:16][CH2:17][CH3:18]>>[C:1]1([CH:6]=[CH:5][C:14]([OH:12])=[CH:3][CH:2]=1)[OH:19].[CH2:15]([O:19][CH2:5][CH2:6][CH2:1][CH3:11])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 178418582HCID 178418582, compound

Product 1

HCID 20329903HCID 20329903, compoundYield 60%

Procedure

100 g of cyclohexene-(1)-dione-(3,6)-tetramethyl ketal were dissolved in 1500 g of n-butanol at 20° C. and the batch was acidified while stirring with 0.005 g of p-toluenesulfonic acid. After about 10 minutes the batch was heated for 30 minutes to 90° C., subsequently neutralized with NaOCH3, the formed methanol and the solvent were completely evaporated under slightly reduced pressure and subsequently the reaction product was submitted to a fractionating distillation. 65.3 g of hydroquinone dibutyl ether having a melting point of 46° C. distilled over under a pressure of 5 mm Hg at a temperature of from 125° to 135° C., which corresponded to a yield of 60% of the theory.

Workup

  1. temperatureAfter about 10 minutes the batch was heated for 30 minutes to 90° C.
  2. customthe formed methanol and the solvent were completely evaporated under slightly reduced pressure
  3. distillationsubsequently the reaction product was submitted to a fractionating distillation
  4. distillation65.3 g of hydroquinone dibutyl ether having a melting point of 46° C. distilled over under a pressure of 5 mm Hg at a temperature of from 125° to 135° C., which

Sources & evidence

ORD record
ord-7741b7ec85be468097dc1567e9ee46ca
Source dataset
uspto-grants-1979_07
Patent number
US04160109

Reaction notes

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