(4-Chloro-3-methoxyphenyl)methanol → 4-Chloro-3-methoxybenzaldehyde

HRID 409520Notes

Reaction equation

HRID 409520 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][C:14]=1[O:21][CH3:22]>ClCCl.C(OCC)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][C:14]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 10910038(4-Chloro-3-methoxyphenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 129097254-Chloro-3-methoxybenzaldehydeYield 87.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of pyridinium chlorochromate (1.37 g, 6.34 mmol) in dichloromethane (35 mL) was treated with Celite (2.0 g) and stirred at rt. A solution of (4-chloro-3-methoxyphenyl)methanol (730 mg, 4.23 mmol) in dichloromethane (5 mL) was added in one portion, and the resulting mixture was stirred at rt for 3 h. After this time, the mixture was diluted with diethyl ether, and stirred vigorously. The mixture was then filtered through a pad of silica gel and the collected solids were rinsed with additional diethyl ether. The combined filtrates were concentrated under vacuum to provide 4-chloro-3-methoxybenzaldehyde as a pale tan-yellow solid (630 mg, 87%). 1H NMR (400 MHz, CDCl3) δ ppm 3.98 (s, 3 H) 7.41 (dd, J=7.9, 1.8 Hz, 1 H) 7.45 (d, J=2.0 Hz, 1 H) 7.55 (d, J=7.6 Hz, 1 H) 9.95 (s, 1 H).

Workup

  1. additionwas treated with Celite (2.0 g)
  2. stirringthe resulting mixture was stirred at rt for 3 h
  3. stirringstirred vigorously
  4. filtrationThe mixture was then filtered through a pad of silica gel
  5. washthe collected solids were rinsed with additional diethyl ether
  6. concentrationThe combined filtrates were concentrated under vacuum

Sources & evidence

ORD record
ord-ede66650577a4b24bdbeb68f8ae83f25
Source dataset
uspto-grants-2014_06
Patent number
US08759390B2

Reaction notes

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