Sodium Hydroxide → HCID 6483399, compound

HRID 2354999Notes

Reaction equation

HRID 2354999 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:17])[C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([O:13][CH:14]([CH3:16])[CH3:15])[CH:7]=1>CO>[OH:12][C:10]1[CH:9]=[C:8]([O:13][CH:14]([CH3:16])[CH3:15])[CH:7]=[C:6]([CH:11]=1)[C:5]([OH:17])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoate

Product 1

HCID 6483399HCID 6483399, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After adding 10 ml of 4N aqueous sodium hydroxide solution to a solution of the 3.0 g (14.3 mmol) of 5-hydroxy-3-isopropoxybenzoic acid methyl ester obtained in Production Example 59 in methanol (50 ml), the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and then saturated aqueous ammonium chloride was added, extraction was performed with chloroform, and the organic layer was dried and then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform:methanol=50:1) to obtain 2.44 g of 5-hydroxy-3-isopropoxybenzoic acid (yield: 87%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionsaturated aqueous ammonium chloride was added
  3. extractionextraction
  4. customthe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-82d1369eb524469fa37866580e09a85c
Source dataset
uspto-grants-2010_07
Patent number
US07754743B2

Reaction notes

Loading…