Methanol → Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

HRID 733516Notes

Reaction equation

HRID 733516 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:19]O>>[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([O:14][CH3:19])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 147565478-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 10987358Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylateYield 94%

Procedure

To a solution of 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (16 g, 0.084 mol) in MeOH was added thionylchloride (23 g, 0.2 mol). The mixture was then stirred at rt for 12 h. The solvent was removed under vacuum and the residue was taken up in EtOAc (200 ml). The organic layer was washed with a 10% aqueous solution of NaHCO3, dried over MgSO4 and evaporated to give 16 g (94%) of the titled compound as a liquid. TLC: Chloroform/MeOH (9/1), Rf=0.9.

Workup

  1. customThe solvent was removed under vacuum
  2. washThe organic layer was washed with a 10% aqueous solution of NaHCO3
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-eefb9bdb155540fbb5ebce5d8c972814
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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