Pyridine → Benzyl 5-acetoxymethyl-2-methoxybenzoate

HRID 1634523Notes

Reaction equation

HRID 1634523 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[C:7]([CH:18]=1)[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(Cl)Cl>[C:27]([O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[C:7]([CH:18]=1)[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18678026Benzyl 5-hydroxymethyl-2-methoxybenzoate

Product 1

HCID 18678020Benzyl 5-acetoxymethyl-2-methoxybenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Next, benzyl 5-hydroxymethyl-2-methoxybenzoate and 100 ml of methylene chloride were mixed and, after pyridine (660 ml, 8.16 mmol), acetic anhydride (460 ml, 4.88 mmol) and N,N-dimethylaminopyridine (25 mg, 0.205 mmol) were added under stirring and cooling with ice, the mixture was stirred overnight. The reaction mixture was washed with 1 mol/l hydrochloric acid, aqueous solution of sodium hydrogencarbonate and brine, then dried over anhydrous sodium sulfate and concentrated to obtain 1.27 g (99%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling with ice
  2. stirringthe mixture was stirred overnight
  3. washThe reaction mixture was washed with 1 mol/l hydrochloric acid, aqueous solution of sodium hydrogencarbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a60a675b768f442f837e9d0a6d660af8
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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