2,2-Dimethoxypropane → Benzoic Acid

HRID 1757070Notes

Reaction equation

HRID 1757070 reaction equation
COC(OC)(C)C.[C@H]1(OC2C=CC=CC=2[C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:30]([OH:32])(=[O:31])[C:29]1[CH:33]=[CH:34][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 10523551HCID 10523551, compound

Product 1

HCID 243Benzoic AcidYield 400.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetone (5.6 ml) and dimethoxypropane (5.6 ml) were added to 4-(2-(α-D-mannopyranosyloxy) phenyl)benzoic acid (0.54 g, 1.43 mmol) to form a heterogeneous mixture. A catalytic amount of p-toluenesulfonic acid monohydrate was introduced and the reaction was stirred at room temperature for 45 minutes, at which point a clear, homogeneous solution was obtained. The solvent was removed in vacuo and the yellow oily residue taken up in ethyl acetate, washed with saturated sodium bicarbonate then saturated sodium chloride, dried (MgSO4) and concentrated in vacuo to afford 4-(2-(2,3:4,6-di-O-isopropylidene)α-D-mannopyranosyloxy)phenyl)benzoic acid (0.70 g).

Workup

  1. customto form a heterogeneous mixture
  2. customwas obtained
  3. customThe solvent was removed in vacuo
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialsaturated sodium chloride, dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-537e52ddea984e7395a4a3da33390a63
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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