Sodium Hydroxide → HCID 66907265, compound

HRID 709567Notes

Reaction equation

HRID 709567 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-28bf5e4f1a894d00b5667958bb792737
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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