Sodium Hydroxide → HCID 14207577, compound

HRID 1360328Notes

Reaction equation

HRID 1360328 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:7]([C:8]([O:10]C)=[O:9])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([CH3:17])[CH:4]=1.[OH-].[Na+]>COCCOC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:17])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10879167Dimethyl 5-methoxy-3-methylphthalate

Product 1

HCID 14207577HCID 14207577, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of compound L (50.0 g, 210 mmol) in 1,2-dimethoxyethane (260 mL) was added 8% aqueous NaOH (262 mL) at 0° C. The mixture was stirred at room temperature for 1 hour, washed with ethyl acetate and acidified to pH 2 using 3 mol/L HCl. The precipitate was filtered and washed with water to give compound M (40.0 g). The filtrate was extracted with ethyl acetate 3 times. The combined organic layers were washed with saturated brine and dried over anhydrous Na2SO4. Filtration and evaporation of the solvent gave compound M (5.47, 96% total yield) as a white powder. 1H NMR (CDCl3, 400 MHz): δ 2.35 (3H, s), 3.86 (3H, s), 3.90 (3H, s), 6.97 (1H, d, J=2.4 Hz), 7.39 (1H, d, J=2.4 Hz). EIMS (+): 224 [M]+

Workup

  1. washwashed with ethyl acetate
  2. filtrationThe precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-a737513a492646dc8ac405bef29f1158
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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