Sulfuric Acid → Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-1-carboxylate

HRID 1176599Notes

Reaction equation

HRID 1176599 reaction equation
[O:1]=[C:2]1[C:11]2[C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.OS(O)(=O)=O.[C:20](=O)([O-])O.[Na+]>CO>[O:1]=[C:2]1[C:11]2[C:10]([C:12]([O:14][CH3:20])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 126763958-Oxo-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid

Product 1

HCID 10867421Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.466 g of 8-oxo-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid in 30 ml of methanol is admixed with 1.850 ml of conc. H2SO4 and the reaction solution is subsequently heated to reflux over 18 hours. The reaction solution is subsequently cooled and poured onto 200 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with 2×200 ml of ethyl acetate. The combined organic phases are washed with 150 ml of saturated aqueous sodium hydrogencarbonate solution and 150 ml of water, dried over sodium sulphate and concentrated. The crude product is obtained as a brown oil and is used without further purification. Rt=3.42

Workup

  1. temperaturethe reaction solution is subsequently heated
  2. temperatureto reflux over 18 hours
  3. temperatureThe reaction solution is subsequently cooled
  4. extractionextracted with 2×200 ml of ethyl acetate
  5. washThe combined organic phases are washed with 150 ml of saturated aqueous sodium hydrogencarbonate solution and 150 ml of water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b8365b9558a24078ba814eebed03db45
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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