Methanol → Dimethyl 4-hydroxyisophthalate

HRID 423264

Reaction equation

HRID 423264 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[C:19](=O)(O)[O-].[Na+].[CH3:24][OH:25]>O>[CH3:24][O:25][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([C:11]([O:13][CH3:19])=[O:12])[CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 124904-Hydroxyisophthalic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 80087Dimethyl 4-hydroxyisophthalate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-hydroxyisophthalic acid (16.0 g) in methanol (150 mL) was added conc. sulfuric acid (5 mL), and the mixture was heated for 22 hours under reflux. Then, the reaction solution was allowed to stand for cooling down to room temperature, diluted with water (150 mL), and added with sodium bicarbonate (15 g). The resulting precipitate was filtered, washed successively with water/methanol (1:1, v/v) (150 mL) and water, and dried to give the title compound (17.45 g).

Workup

  1. temperaturethe mixture was heated for 22 hours
  2. temperatureunder reflux
  3. filtrationThe resulting precipitate was filtered
  4. washwashed successively with water/methanol (1:1
  5. dry with materialv/v) (150 mL) and water, and dried

Sources & evidence

ORD record
ord-30654b4550c94ee293b82d838b3f59c9
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Linked notes

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