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

HRID 1506781Notes

Reaction equation

HRID 1506781 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8](=[CH:14][C:15]([OH:17])=[O:16])[CH2:7][CH2:6]2.O>C(O)(=O)C.O.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH2:14][C:15]([OH:17])=[O:16])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 962WaterHCID 730967892-(3,4-Dihydro-6-methoxy-1-oxo-2(1H)-naphthalenylidene)acetic acid

Product 1

HCID 13574088(6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acidYield 79.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

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)+.

Workup

  1. filtrationThe reaction mixture was then filtered over celite bed
  2. customthe organic layer was removed under reduced pressure
  3. customto give a residue
  4. filtrationThe resulting solids were filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c8d40d761ec14dc1ae35e3a31188e4c0
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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