p-Toluenesulfonic acid → HCID 23460412, compound

HRID 2286816Notes

Reaction equation

HRID 2286816 reaction equation
[CH3:1][O:2][CH:3]([O:5][CH3:6])[CH3:4].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1>CCOCC>[CH3:4][CH:3]1[O:5][CH2:6][CH2:17][CH:7]2[CH:1]([CH2:9][CH2:8][CH2:7][CH2:12][CH2:11][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[O:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 107951,1-Dimethoxyethane

Product 1

HCID 23460412HCID 23460412, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 240 gm (1 mol) of the diol prepared according to (c) above, 90 gm (1 mol) of acetaldehyde dimethyl acetal, and 0.2 gm of p-toluene sulfonic acid was refluxed for five hours at 70° C. After the reaction was completed, the reaction mixture was taken up in ether, washed neutral with 2 N sodium hydroxide solution, washed with water, and then dried over anhydrous sodium sulfate. The ether and methanol were distilled off, and then the residue was distilled in the oil-pump vacuum. The 14-methyl-13,15-dioxabicyclo[10.5.0]heptadecane obtained was a colorless liquid with the following characteristics:

Workup

  1. customprepared
  2. washwashed neutral with 2 N sodium hydroxide solution
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe ether and methanol were distilled off
  6. distillationthe residue was distilled in the oil-pump vacuum

Sources & evidence

ORD record
ord-c51f500e4fa64606aa85ed63f3198321
Source dataset
uspto-grants-1981_05
Patent number
US04268443

Reaction notes

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