Acetic Acid → ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1457318Notes

Reaction equation

[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[H-].[Na+].[C:11]1(=[O:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1.C(O)(=O)C>C1(C)C=CC=CC=1>[O:21]=[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH:12]1[C:1]([O:5][CH2:6][CH3:7])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of diethyl carbonate (200 g) in toluene (800 ml) was added 60% sodium hydride (27.4 g), and the mixture was stirred at 50° C. for 30 minutes, and thereto was added dropwise a solution of 3,4-dihydro-1(2H)-napthalenone (50 g) in toluene (200 ml). The mixture was refluxed for one hour, and poured into ice-water, and the mixture was neutralized with acetic acid. The toluene layer was collected, washed successively with an aqueous potassium carbonate solution and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by distillation under reduced pressure to give ethyl 1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate (47 g) as an oily product, b.p. 135°-145° C./2 mmHg.

Workup

temperatureThe mixture was refluxed for one hour
customThe toluene layer was collected
washwashed successively with an aqueous potassium carbonate solution and water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
distillationThe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record: ord-ccd3562d52f5491f91209436dbc6d95f
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05847159

Reaction notes

Loading…