Dimethyl Sulfoxide → HCID 12740094, compound

HRID 2221135Notes

Reaction equation

HRID 2221135 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:23]=[CH:22][C:15]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)C>[Cl:11][C:12]1[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22247647HCID 22247647, compound

Product 1

HCID 12740094HCID 12740094, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalylchloride (1.0 ml, 0.011 mmol) is added to a solution of dimethylsulfoxide (DMSO) (1.7 ml, 0.022 mol) in methylenechloride (20 ml) at −60° C. 1-(4-Chlorophenoxy)-butan-2-ol (2.0 g, 0.01 mol) is added in one portion. After 15 minutes triethylamine (7 ml, 0.05 mol) is added and the reaction temperature is allowed to warm up and reach 0° C. The mixture is diluted with diethylether and washed repeatedly with brine. The organic phase is dried, filtered evaporated to give the 1-(4-chlorophenoxy)-butane-2-one.

Workup

  1. temperatureto warm up
  2. customreach 0° C
  3. washwashed repeatedly with brine
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-64955e0759ce487eafd1d17d4dfb6f83
Source dataset
uspto-grants-2008_05
Patent number
US07368479B2

Reaction notes

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