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

HRID 1596762Notes

Reaction equation

HRID 1596762 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-methylthiochromane-7-carboxylate are heated below boiling point for 4 hours in 60 ml of ethanol with 1 g of sulfuric acid added. The solvent is then distilled off and the residue is taken up in water. The aqueous phase is extracted using ethyl acetate. The organic phase is washed using sodium hydrogen carbonate solution, dried and concentrated. The product is purified by chromatography.

Workup

  1. customfor 4 hours
  2. additionadded
  3. distillationThe solvent is then distilled off
  4. extractionThe aqueous phase is extracted
  5. washThe organic phase is washed
  6. customdried
  7. concentrationconcentrated
  8. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-f909f686aad041baba756bbb7699a757
Source dataset
uspto-grants-2001_09
Patent number
US06291682B1

Reaction notes

Loading…