Water → 1-(2-Methoxy-4-methylphenyl)propan-1-one

HRID 1671359Notes

Reaction equation

HRID 1671359 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O.[CH3:24][O:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=1[CH:33]([OH:36])[CH2:34][CH3:35]>C(Cl)Cl>[CH3:24][O:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=1[C:33](=[O:36])[CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 672125481-(2-Methoxy-4-methyl-phenyl)-propan-1-ol

Product 1

HCID 42837091-(2-Methoxy-4-methylphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dess-Martin periodinane (2.89 g, 6.82 mmol) and H2O (0.123 ml, 6.82 mmol) are added to DCM (20 ml) and left to stir for 10 minutes. This mixture is treated with 1-(2-methoxy-4-methyl-phenyl)-propan-1-ol (step 1) (1.17 g, 6.49 mmol) in DCM (15 ml) and stirred for 1 hour. The reaction mixture is diluted with DCM and washed with Na2S2O3, NaHCO3, water, brine, dried (MgSO4) and concentrated under vacuum to yield the title product as a clear oil; 1H NMR (400 MHz, CDCl3) δ 7.64 (d, 1H), 6.82 (d, 1H), 6.77 (s, 1H), 3.90 (s, 3H), 3.00 (q, 2H), 2.39 (s, 3H), 1.17 (t, 3H).

Workup

  1. waitleft
  2. stirringstirred for 1 hour
  3. washwashed with Na2S2O3, NaHCO3, water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a44b1d32402647f7941e34f5d3be467b
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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