Reaktion #1593963

Reaktionsgleichung

Water

1A

2-(6-Methoxy-1-oxo-3,4-dihydronaphthalen-2(1H)-ylidene)acetic acid

→

title compound

Ausbeute 79.3%

2-(6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid

Ausbeute 79.3%

Lösungsmittel

acetic acid water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was then filtered over celite bed
2. 2
   Sonstigethe organic layer was removed under reduced pressure
3. 3
   Sonstigeto give a residue
4. 4
   FiltrationThe resulting solids were filtered off
5. 5
   Sonstigedried under vacuum

Vorschrift

Zinc (493 g, 7536 mmol) was added to a solution of 1A (350 g, 1507 mmol) in acetic acid-water mixture (1 L+420 mL), and the mixture was stirred at 100° C. for 3 h. The reaction mixture was then filtered over celite bed, and the organic layer was removed under reduced pressure to give a residue. Water (5 L) was added to the residue. The resulting solids were filtered off and dried under vacuum to afford the title compound (280 g, 77%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 12.2 (bs, 1H), 7.8 (d, J=8.4 Hz, 1H), 6.9 (m, 2H), 3.8 (s, 3H), 3.1 (m, 1H), 3.0-2.8 (m, 2H), 2.7 (m, 1H), 2.4 (m, 1H), 2.2 (m, 1H), 1.9 (m, 1H). ESI-MS m/z: 235 (M+H)+.

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