Water → 2-Methyl-2-phenylpropanal

HRID 1810053Notes

Reaction equation

HRID 1810053 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.N1C=CC=CC=1.O>CS(C)=O>[CH3:5][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:1])[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8471TriethylamineHCID 219535beta,beta-Dimethylbenzeneethanol

Product 1

HCID 2838792-Methyl-2-phenylpropanalYield 91.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-methyl-2-phenyl-propan-1-ol (13.3 g, 87.0 mmol) in DMSO (150 mL) was added triethylamine (24.7 mL, 178.0 mmo) at rt, followed by pyridine sulfuric oxide (28.6 g, 180.0 mmol). The mixture was stirred for 2.5 h at rt. Water was added and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product 2-methyl-2-phenyl-propionaldehyde (12.0 mg, 91.6%), which was used to the next step without further purification.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2bacee6f3a5a418ea303bb1ae90ae687
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

Loading…