Water → 4-Methoxyphenyl benzoate

HRID 871977Notes

Reaction equation

HRID 871977 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)(Cl)Cl.[OH2:30]>ClCCl>[C:17]([O:24][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)(=[O:30])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 90154-Methoxyphenol

Product 1

HCID 1370594-Methoxyphenyl benzoateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxyanisole (1.25 g, 10.1 mmol) was dissolved in anhydrous dichloromethane (10 mL), and triethylamine (4.25 mL, 30.5 mmol) and benzoyl chloride (1.40 mL, 12.1 mmol) were added thereto successively. The reaction mixture was stirred at room temperature for 4 hours. Chloroform (50 mL) and water (50 mL) were added to the reaction mixture and partitioned. The organic layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was filtered with hexane (50 mL) to give the titled reference compound (2.24 g) as a colorless solid. (Yield 98%)

Workup

  1. custompartitioned
  2. washThe organic layer was washed with saturated brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. filtrationThe obtained residue was filtered with hexane (50 mL)

Sources & evidence

ORD record
ord-7cf3ef4c7ffa436893aae22bd0b3e67f
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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