p-Toluenesulfonic acid → HCID 54550798, compound

HRID 2071660Notes

Reaction equation

HRID 2071660 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH:16](OC)[O:17]C)[O:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[O:12]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54015276HCID 54015276, compound

Product 1

HCID 54550798HCID 54550798, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
60 °C

Procedure

8-(5-Dimethoxymethyl-tetrahydro-2-furyl)-octanoic acid methyl ester (I) (1.51 g, 0.00500 mole), p-toluene-sulfonic acid (30 mg), and acetone (50 ml) were stirred and heated for about 6 hours in such a way that every 30 minutes about 30 ml of the acetone were distilled off, and a similar new portion of acetone was added to the reaction mixture. The reaction was followed by thin layer chromatography (tlc). After cooling, sodium bicarbonate (0.1 g) was added, and the suspension was stirred for 1 hour. After filtration, the solvent was removed by heating on a water bath (60° C, 10 mmHg), and the residual yellow oil (1.45 g) was purified by distillation, giving 1.00 g (78%) of II as a colourless oil, b0.05 119°-122° C, nD25 1.4603.

Workup

  1. distillationwere distilled off
  2. additiona similar new portion of acetone was added to the reaction mixture
  3. temperatureAfter cooling
  4. additionsodium bicarbonate (0.1 g) was added
  5. filtrationAfter filtration
  6. customthe solvent was removed
  7. distillationthe residual yellow oil (1.45 g) was purified by distillation

Sources & evidence

ORD record
ord-43f7a64a5eb14989aa1fd21cc4c43070
Source dataset
uspto-grants-1977_09
Patent number
US04048198

Reaction notes

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