Triacetoxyperiodinane → 4-{1-[4-(3,3-Dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzoic acid

HRID 502064Notes

Reaction equation

HRID 502064 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[CH:3]([OH:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH3:26])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:27].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[CH3:30][C:2]([CH3:1])([CH3:29])[C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH3:26])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:27]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 103643684-{1-[4-(3,3-Dimethyl-2-hydroxybutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzoic acid

Product 1

HCID 103642554-{1-[4-(3,3-Dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-{1-[4-(3,3-dimethyl-2-hydroxybutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzoic acid, Example 1, (0.50 g, 1.22 mmol) in CH2Cl2 (10 mL) is added a solution of the Dess-Martin reagent (0.57 g, 1.34 mmol) in CH2CL2 (10 mL) dropwise and stirred for 2 h. The reaction is diluted with EtOAc (100 mL), washed with 10% Na2SO3 (2×20 ml), 0.1 M HCl (20 ml), and H2O (20 ml). The organic layer is MgSO4 dried, and concentrated to give the title compound (0.48 g, 1.17 mmol, 95%).

Workup

  1. washwashed with 10% Na2SO3 (2×20 ml), 0.1 M HCl (20 ml), and H2O (20 ml)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b19dd7b355234c45862b098dbef5cb5b
Source dataset
uspto-grants-2010_08
Patent number
US07772425B2

Reaction notes

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