Ethanol → Methyl 4-ethoxy-8-methylthiochroman-7-carboxylate

HRID 1005293Notes

Reaction equation

HRID 1005293 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[C:7]([CH3:16])[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[CH2:22]([O:1][CH:2]1[C:11]2[C:6](=[C:7]([CH3:16])[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1)[CH3:23]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 15335230Methyl 4-hydroxy-8-methylthiochroman-7-carboxylate

Product 1

HCID 15335231Methyl 4-ethoxy-8-methylthiochroman-7-carboxylate

Procedure

13.8 g (0.058 mol) of methyl 4-hydroxy-8-methylthiochroman-7-carboxylate are heated at boiling point for 4 hours in 60 ml of ethanol with addition of 1 g of sulfuric acid. The solvent is then distilled off and the residue is taken up with water. The aqueous phase is extracted with ethyl acetate. The organic phase is washed with sodium hydrogen carbonate solution, dried and concentrated. The product is purified by chromatography.

Workup

  1. customfor 4 hours
  2. distillationThe solvent is then distilled off
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washThe organic phase is washed with sodium hydrogen carbonate solution
  5. customdried
  6. concentrationconcentrated
  7. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-27caee5b8b204f3480500da684086e85
Source dataset
uspto-grants-2000_04
Patent number
US06054414

Reaction notes

Loading…