Catechol → o-Hydroxyphenyl benzoate

HRID 1882191Notes

Reaction equation

HRID 1882191 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1([C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10])[OH:8].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O>[C:15]([O:8][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[OH:10])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 289CatecholHCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 79984o-Hydroxyphenyl benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium carbonate (63.6 g) was added to a solution of pyrocatechol (55 g) in water (230 mL), and to the resulting mixture was added dropwise benzoyl chloride (58 mL) over a period of 2 hours with vigorous stirring. The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was acidified carefully by dropwise addition of 2N hydrochloric acid (350 mL) and then extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from a mixed solvent of ethyl acetate (100 mL) and n-hexane (400 mL) to give the title compound (64.6 g) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from a mixed solvent of ethyl acetate (100 mL) and n-hexane (400 mL)

Sources & evidence

ORD record
ord-e93b87fec1834d0e97e808444840d01c
Source dataset
uspto-grants-2012_11
Patent number
US08318952B2

Reaction notes

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