Ethanol → HCID 10084055, compound

HRID 1506782Notes

Reaction equation

HRID 1506782 reaction equation
CS(O)(=O)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[CH:13]([CH2:19][C:20]([OH:22])=[O:21])[CH2:12][CH2:11]2.[CH2:23](O)[CH3:24]>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[CH:13]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:12][CH2:11]2

Participants

4

Reactant 3

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 13574088(6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid

Product 1

HCID 10084055HCID 10084055, compoundYield 81%

Procedure

Methane sulfonic acid (450 mL) was added to a solution of 1B (250 g, 1067 mmol) in ethanol (1.5 L), and the mixture was stirred at room temperature for 16 h. Ethanol was removed from the reaction mixture under reduced pressure, and residue was diluted with ethyl acetate and extracted with brine solution. The organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated under vacuum to afford the title compound (241 g, 81%) as a solid. 1H NMR (400 MHz, CDCl3): δ 7.99 (d, J=8.8 Hz, 1H), 6.82 (dd, J1=2.4 Hz, J2=8.8 Hz, 1H), 6.68 (d, J=2.4 Hz, 1H), 4.18 (q, J=8.1 Hz, 2H), 3.8 (s, 3H), 3.12-2.85 (m, 4H), 2.39 (q, J=9.0 Hz, 1H), 2.23 (m, 1H), 1.94 (dq, J1=4.5 Hz, J2=12.6 Hz, 1H), 1.28 (t, J=7.5 Hz, 3H). ESI-MS m/z: 263 (M+H)+.

Workup

  1. customEthanol was removed from the reaction mixture under reduced pressure, and residue
  2. additionwas diluted with ethyl acetate
  3. extractionextracted with brine solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-564dbf374a964794a17bbcdb4c7e2cc9
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

Loading…