1-Chloro-2-methoxy-4-methylbenzene → 4-Chloro-3-methoxybenzaldehyde

HRID 734749Notes

Reaction equation

HRID 734749 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].CC(O)=[O:13].O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:13])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 993521-Chloro-2-methoxy-4-methylbenzeneHCID 21899381Acetic acid--water (1/1)2×

Product 1

HCID 129097254-Chloro-3-methoxybenzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ceric ammonium nitrate (43.3 g, 79.0 mmol, 4.00 equiv) was dissolved in 1:1 HOAc/H2O (200 mL). This solution was added dropwise over one hour to a stirred solution of the product from Step 1 (3.09 g, 19.7 mmol, 1.00 equiv) in 1:1 HOAc/H2O (100 mL) at 100° C. After the addition was complete, the reaction was stirred for an additional 15 minutes. The reaction was cooled, diluted with H2O and extracted twice with Et2O. The combined organic extracts were washed three times with H2O, three times with satd. NaHCO3, and once with brine. The organic phase was dried over MgSO4 and concentrated en vacuo to afford the title compound (3.00 g, 89%) as an amber oil. 1H NMR (400 MHz, CDCL3) 9.97 (s, 1H), 7.57 (d, 1H), 7.46 (s, 1H), 7.43 (d, 1H), 4.00 (s, 3H).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was cooled
  3. extractionextracted twice with Et2O
  4. washThe combined organic extracts were washed three times with H2O, three times with satd
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated en vacuo

Sources & evidence

ORD record
ord-fa2997c126424bbe8b084fbde9bfe0a7
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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