Sodium Hydroxide → HCID 18988219, compound

HRID 2396128Notes

Reaction equation

HRID 2396128 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

Procedure

Part B. A solution of the ester prepared in Part A above (1.68 g, 6.31 mmol) in ethanolic sodium hydroxide (60.0 mL, 0.25M in 95% ethanol, 15.0 mmol) was stirred at ambient temperature for 14 hours. The solution was evaporated, and the residue neutralized to pH 5 with 1N aqueous hydrochloric acid. This was diluted to 100 mL with water, and extracted with ethyl acetate (2×100 mL). The extracts were washed with brine, 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 an oil (1.42 g, 5.96 mmol, 94%). 1H NMR (CDCl3): δ 7.06 (1H, s); 6.62 (1H, s); 5.30 (1H, s); 4.34-4.24 (1H, m); 4.02-3.92 (1H, m);3.87 (6H, s); 2.94-2.72 (2H, m). Mass spectrum (NH3 -CI/DDIP): m/z 241(2%); 240 (11%); 239 (87%); 221 (8%); 193 (100%).

Workup

  1. customThe solution was evaporated
  2. additionThis was diluted to 100 mL with water
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-25e2c2c2136d4682aa4da139c762f573
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

Loading…