Water → 2-Methyl-2-phenylpropanal

HRID 704419

Reaction equation

HRID 704419 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH2:9][OH:10].C(N(CC)CC)C.O>ClCCl>[CH3:11][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:7])[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 219535beta,beta-Dimethylbenzeneethanol

Product 1

HCID 2838792-Methyl-2-phenylpropanalYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalylchloride (4.1 ml) in dichloromethane (100 ml) was added dropwise a solution of dimethylsufoxide (7.14 g) in dichloromethane (10 ml) at -60° C., and the mixture was stirred for 10 minutes. To the resultant mixture was added a solution of 2-methyl-2-phenylpropanol (6.16 g) in dichloromethane (15 ml) at the same temperature. After stirring for one hour, to the mixture was added triethylamine (20.7 g). The mixture was further stirred for 30 minutes and allowed to room temperature. After adding water, the mixture was extracted with dichloromethane. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel (40 g) column chromatography and elution with 2% ethyl acetate hexane solution gave 4.93 g of 2-methyl-2-phenylpropanal.

Workup

  1. stirringAfter stirring for one hour, to the mixture
  2. stirringThe mixture was further stirred for 30 minutes
  3. customallowed to room temperature
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe resultant residue was subjected to silica gel (40 g) column chromatography and elution with 2% ethyl acetate hexane solution

Sources & evidence

ORD record
ord-5d6c495eb6e5443890604fe49e7c2e0d
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Linked notes

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