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

HRID 1368223

Reaction equation

HRID 1368223 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].N1C=CC=CC=1.[Cl:14][C:15]1C=C(O)[CH:18]=[CH:19][C:20]=1[CH3:21]>CCOCC>[C:5]([O:4][C:1]1[CH:18]=[CH:19][C:20]([CH3:21])=[C:15]([Cl:14])[CH:2]=1)(=[O:7])[CH3:6]

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

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

Workup

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

Sources & evidence

ORD record
ord-98408229a3b940c89a78ad89c4f7eae1
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Linked notes

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