Dimethyl Sulfoxide → 3-(3-Chlorophenyl)-3-methylbutan-2-one

HRID 1627353Notes

Reaction equation

HRID 1627353 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C:18]([CH3:23])([CH3:22])[CH:19]([OH:21])[CH3:20])[CH:15]=[CH:16][CH:17]=1.CCN(CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([C:18]([CH3:23])([CH3:22])[C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 667407143-(3-Chlorophenyl)-3-methylbutan-2-ol

Product 1

HCID 242739623-(3-Chlorophenyl)-3-methylbutan-2-oneYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of oxalyl chloride (3.4 mL, 40 mmol, 2 eq) in CH2Cl2 (100 mL) at −78° C. was added DMSO (4.9 mL, 70 mmol, 3.5 eq) dropwide. After stirring 1 h, the reaction mixture was treated dropwise with a solution of 3-(3-chlorophenyl)-3-methylbutan-2-ol (3.98 g, 20 mmol) in CH2Cl2 (100 mL). After stirring 1 h, Et3N (13.9 mL, 100 mmol, 5 eq) was added to the reaction mixture and the resulting mixture was slowly warmed to room temperature. The reaction mixture was partitioned in CH2Cl2 and water. The organic layer was separated, washed with 1N HCl and water, dried over MgSO4 and evaporated in vacuo to give 3-(3-chlorophenyl)-3-methylbutan-2-one (3.9 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.29 (m, 3H), 7.13 (m, 1H), 1.97 (s, 3H), 1.47 (s, 6H).

Workup

  1. stirringAfter stirring 1 h
  2. customThe reaction mixture was partitioned in CH2Cl2
  3. customThe organic layer was separated
  4. washwashed with 1N HCl and water
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c40bc163500247ef901d272f08df84a8
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

Loading…