Water → 3,3-Dimethyl-1-phenylhex-5-en-2-one

HRID 325187Notes

Reaction equation

HRID 325187 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:12][CH:13]=[CH2:14])[CH:3]([OH:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.O>C(Cl)Cl.CS(C)=O>[CH3:1][C:2]([CH3:15])([CH2:12][CH:13]=[CH2:14])[C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 81531DiisopropylethylamineHCID 146174373,3-Dimethyl-1-phenylhex-5-en-2-ol

Product 1

HCID 153393703,3-Dimethyl-1-phenylhex-5-en-2-oneYield 101%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step 1 (15 g) and 50 mL of i-Pr2NEt in 250 mL of CH2Cl2 cooled at 0° C. was added dropwise a solution of sulfur trioxide pyridine complex (23.8 g) in 100 mL of DMSO. After stirring for 10 min, the reaction mixture was treated with 200 mL H2O and extracted with 200 mL of 1:1 EtOAc/hexane. The extract was dried over MgSO4 and concentrated to give 15 g of the title compound as a yellow oil.

Workup

  1. extractionextracted with 200 mL of 1:1 EtOAc/hexane
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4b14bef825d34615b513de3b60b018a5
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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