p-Toluenesulfonic acid → HCID 19010986, compound

HRID 1741964Notes

Reaction equation

HRID 1741964 reaction equation
CC1(C)[O:19][CH:5]2[CH:6]3[CH2:11][O:10][C:9](=[O:12])[CH:8]=[C:7]3[CH2:13][CH:14]([O:15]COC)[CH:4]2[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO.O>[OH:15][CH:14]1[CH2:13][C:7]2=[CH:8][C:9](=[O:12])[O:10][CH2:11][CH:6]2[CH:5]([OH:19])[CH:4]1[OH:3]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 19010990HCID 19010990, compound

Product 1

HCID 19010986HCID 19010986, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1,5,6,7,8,8a-Hexahydro-7,8-(dimethylmethylenedioxy)-6-methoxymethoxy-3H-2-benzopyran-3-one (284 mg) was dissolved in 50 ml of methanol and 5 ml of water, and a catalytic amount of p-toluenesulfonic acid was added. The mixture was refluxed for 1 hour. After cooling, the reaction mixture was poured into a sodium hydrogen carbonate aqueous solution and extracted with diethyl ether. The extract was washed with a sodium chloride aqueous solution, dried, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain 114 mg of 1,5,6,7,8,8a-hexahydro-6,7,8-trihydroxy-3H-2-benzopyran-3-one having the following property (yield 57%).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with a sodium chloride aqueous solution
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ab356729a8c94cc4bd70b5efe54d9496
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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