m-Chloroperbenzoic acid → 3-Chloro-4-methoxyphenol

HRID 493199

Reaction equation

HRID 493199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])C=O.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([OH:20])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 786193-Chloro-4-methoxybenzaldehyde

Product 1

HCID 130819293-Chloro-4-methoxyphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-4-methoxybenzaldehyde (2.50 g, 15.0 mmol) was dissolved in 30 mL of CH2Cl2, treated with 3-chloro-perbenzoic acid (4.84 g, 70%, 1.4 eq.), and then kept for 3.5 h at ambient temperature. Pouring onto crashed ice/pyrosulfite-solution, twofold extraction with AcOEt, washing with Na2CO3-solution, drying over sodium sulfate, and evaporation of the solvents left 2.89 g of the intermediate formiate which was hydrolysed by stirring for 20 Min. in 25 mL of MeOH containing 2.113 g of K2CO3. Standard extractive work-up delivered then 2.60 g of the title compound sufficiently pure for the next step.

Workup

  1. additionPouring
  2. extractionextraction with AcOEt
  3. washwashing with Na2CO3-solution
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  5. waitleft 2.89 g of the intermediate formiate which

Sources & evidence

ORD record
ord-505e7521ca5e48a286cf7ad831906891
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Linked notes

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