Sodium Hydroxide → HCID 58780911, compound

HRID 732523Notes

Reaction equation

HRID 732523 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Na+]>CO.O.C(OCC)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:13]=[C:12]([O:14][CH:15]([CH3:16])[CH3:17])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 23072939HCID 23072939, compound

Product 1

HCID 58780911HCID 58780911, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Stir 5-isopropoxy-isophthalic acid dimethyl ester (3.7 g, 14.7 mmol) and NaOH (0.56 g, 14 mmol) in methanol (100 mL) and water (2 mL) overnight at room temperature. Concentrate methanol and redissolve the residue in diethyl ether (100 mL) and water (100 mL). Separate the layers and wash with diethyl ether. Concentrate the diethyl ether layer and recover 5-isopropoxy-isophthalic acid dimethyl ester (0.45 g). Acidify the aqueous layer with 5 N HCl to about pH=2, extract with ethyl acetate (3×50 mL). Wash the combined organic layers with saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give the title compound (3.0 g, 86%).

Workup

  1. customSeparate the layers
  2. washwash with diethyl ether
  3. concentrationConcentrate the diethyl ether layer
  4. customrecover 5-isopropoxy-isophthalic acid dimethyl ester (0.45 g)
  5. extractionextract with ethyl acetate (3×50 mL)
  6. washWash the combined organic layers with saturated aqueous sodium chloride
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-3de3d168ddc54b368cab7c732818813a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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