Pyridine → Phenol, 3-chloro-4-methyl-, acetate

HRID 1072928

Reaction equation

HRID 1072928 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:10](OC(=O)C)(=[O:12])[CH3:11].N1C=CC=CC=1>CCOCC>[C:10]([O:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 148533-Chloro-4-methylphenol

Product 1

HCID 538898Phenol, 3-chloro-4-methyl-, acetateYield 99.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-chloro-4-methylphenol (500 mg) in ether (5.0 ml) were added acetic anhydride (430 mg) and pyridine (416 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was washed with 1N hydrochloric acid (once) and saturated brine (twice), dried over magnesium sulfate and concentrated to dryness under reduced pressure to give the objective compound (645 mg) as a pale-yellow oil.

Workup

  1. washThe reaction mixture was washed with 1N hydrochloric acid (once) and saturated brine (twice),
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cbe50be0c22e43b4bae2b464b757fed7
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Linked notes

Loading…