Sodium Hydroxide → HCID 18988219, compound

HRID 2396126Notes

Reaction equation

HRID 2396126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([C:15]([O:17]CC)=[O:16])[S:8][CH2:7][CH2:6]2.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([C:15]([OH:17])=[O:16])[S:8][CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 18988278HCID 18988278, compound

Product 1

HCID 18988219HCID 18988219, compound

Conditions

Temperature
0 °C

Procedure

Part D. The ester compound from Part C above (1.88 g, 6.66 mmol) was stirred in ethanolic sodium hydroxide solution (0.25N, 60.0 mL, 15.0 mmol)for 14 hours. The mixture was evaporated, and the residue was taken up in 1N aqueous sodium hydroxide (120 mL). This solution was washed with ether (2×120 mL), then cooled to 0° C. and neutralized to pH 5 with6N aqueous hydrochloric acid. This was then extracted with ethyl acetate (2×120 mL), and the extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the product, 6,7-dimethoxy-1,2,3,4-tetrahydro-2-thianaphthalene-1-carboxylic acid, as asolid, mp 167°-169° C. (1.66 g, 6.53 mmol, 98%). 1H NMR(CDCl3): δ 6.63 (2H, s); 4.43 (1H, s); 3.86 (3H, s); 3.85 (3H, s); 3.34 (1H, ddd, J=13.8, 8.0, 5.2 Hz); 3.09 (1H, dd, J=10, 4.5 Hz); 3.03(1H, dd, J=10, 4.9 Hz); 2.74 (1H, dt, J=13.8, 4.7 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 272 (100%); 256 (1%); 255 (8%); 209 (3%); 106 (1%).

Workup

  1. customThe mixture was evaporated
  2. washThis solution was washed with ether (2×120 mL)
  3. extractionThis was then extracted with ethyl acetate (2×120 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a748ff965f45475e85e15b59b051ce8a
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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