[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-methanol → 4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzaldehyde

HRID 2266062Notes

Reaction equation

HRID 2266062 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH2:22][OH:23])=[C:16]([CH:24]([CH3:32])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:15]=1>C(Cl)Cl.CCOCC>[CH3:12][O:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH:22]=[O:23])=[C:16]([CH:24]([CH3:32])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:15]=1

Participants

5

Reactant 2

HCID 59598568[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 595985844,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzaldehydeYield 76.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyridinium chlorochromate (1.253 g, 5.8 mmol) in 40 mL CH2Cl2 was cooled to 0° C. [4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-methanol (1.110 g, 3.88 mmol) in 5.0 mL CH2Cl2 was added drop-wise and allowed to stir for 45 minutes. The mixture was diluted in 200 mL Et2O, filtered through celite and concentrated in vacuo to afford a dark brown oil. Purification via flash chromatography (9:1 hexane/ethyl acetate) gave 4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzaldehyde (0.840 g, 76%) as a clear oil.

Workup

  1. additionwas added drop-wise
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuo
  4. customto afford a dark brown oil
  5. customPurification via flash chromatography (9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-da817f92d8cf447bbff2d1ab0d7fc4f5
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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