Sodium Hydroxide → HCID 66907265, compound

HRID 1690455Notes

Reaction equation

HRID 1690455 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[CH:24]=[CH:23][C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>>[O:20]1[C:19]2[CH:23]=[CH:24][C:16]([CH2:15][O:14][C:10]3[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:25])=[O:2])[C:5]=3[C:6]([OH:8])=[O:7])=[CH:17][C:18]=2[O:22][CH2:21]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 66906062HCID 66906062, compound

Product 1

HCID 66907265HCID 66907265, compound

Procedure

A solution of 3-(benzo[1,3]dioxol-5-ylmethoxy)-phthalic acid dimethyl ester (1.6 g crude, 4.8 mmol) in reagent alcohol (100 mL) and 3 N sodium hydroxide (35 mL) was refluxed for two hours. The solution was evaporated and the residue was dissolved in water (80 mL) and washed with methylene chloride (3×70 mL) then acidified to pH around 4. The resulting mixture was extracted with ethyl acetate (2×60 mL) and the combined organic layers was washed with water (2×70 mL), dried and concentrated to give 3-(benzo[1,3]dioxol-5-ylmethoxy)-phthalic acid as an off-white solid (1.2 g, 80% crude yield). The product was used in the next step without further purification.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in water (80 mL)
  3. washwashed with methylene chloride (3×70 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×60 mL)
  5. washthe combined organic layers was washed with water (2×70 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a35266e12cb0471890e807ab4fceed09
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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