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

HRID 2181015

Reaction equation

HRID 2181015 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-79eae0ab6e924be499d5289f2e5fa59c
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Linked notes

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