p-Toluenesulfonic acid monohydrate → Methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-3-carboxylate

HRID 862993Notes

Reaction equation

HRID 862993 reaction equation
[O:1]=[C:2]1[C:10]2[C:9]([C:11]([OH:13])=[O:12])=[CH:8][O:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]=[C:2]1[C:10]2[C:9]([C:11]([O:13][CH3:15])=[O:12])=[CH:8][O:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 7139374-Oxo-4,5,6,7-tetrahydro-1-benzofuran-3-carboxylic acid

Product 1

HCID 11499367Methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-3-carboxylateYield 848.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.11 g of 4-oxo-4,5,6,7-tetrahydrobenzo[b]furan-3-carboxylic acid in 100 ml of methanol is added 202 mg of p-toluenesulfonic acid hydrate and the mixture heated at reflux for 24 hours. The reaction mixture is cooled to room temperature and the methanol concentrated in vacuo to a residue. The residue is dissolved in 100 ml of ethyl acetate and washed with 30 ml of saturated sodium bicarbonate and 30 ml of brine. The organic layer is dried with Na2SO4, filtered and the filtrate concentrated in vacuo to a residue which is crystallized from ethyl acetate-hexane to give 1.75 g of the desired product as a white crystalline solid, m.p. 100°-102° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hours
  3. concentrationthe methanol concentrated in vacuo to a residue
  4. dissolutionThe residue is dissolved in 100 ml of ethyl acetate
  5. washwashed with 30 ml of saturated sodium bicarbonate and 30 ml of brine
  6. dry with materialThe organic layer is dried with Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo to a residue which
  9. customis crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c713641f5785420abdc41a666cca5fd9
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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