Acetone → HCID 53710769, compound

HRID 436529Notes

Reaction equation

HRID 436529 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1(OC)[CH2:15][CH2:14][C:13]([O:21]C)([CH:16]([O:19][CH3:20])[O:17][CH3:18])[O:12]1.CC(C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[CH2:15][CH2:14][C:13](=[O:21])[CH:16]([O:19][CH3:20])[O:17][CH3:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 53666704HCID 53666704, compound

Product 1

HCID 53710769HCID 53710769, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-(2,5-Dimethoxy-5-dimethoxymethyl-tetrahydro-2-furyl)-octanoic acid methyl ester (1.00 g, 0.0028 mole), 20 ml of acetone and p-toluenesulfonic acid (0.002 g) were stirred for 2 hours at room temperature. The clear solution was poured into cold water (100 ml, 0° C) and extracted with two 50-ml portions of ether. The combined ethereal extracts were washed with 6% aqueous sodium hydrogen carbonate (30 ml) and then with two 50-ml portions of water, dried with magnesium sulfate, and evaporated to dryness from a water bath (60° C), at last under 15 mm Hg. The distillation of residual oil gave 0.83 g (95%) of the title compound, b0.1 154°-156° C, nD25 1.4531.

Workup

  1. extractionextracted with two 50-ml portions of ether
  2. washThe combined ethereal extracts were washed with 6% aqueous sodium hydrogen carbonate (30 ml)
  3. dry with materialwith two 50-ml portions of water, dried with magnesium sulfate
  4. customevaporated to dryness from a water bath (60° C)
  5. distillationThe distillation of residual oil

Sources & evidence

ORD record
ord-fee2ebcd1d82491fa9a259445884b121
Source dataset
uspto-grants-1977_02
Patent number
US04009187

Reaction notes

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