Dimethyl Sulfoxide → HCID 54403033, compound

HRID 1248992Notes

Reaction equation

HRID 1248992 reaction equation
[C:1](Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([C:17]([CH:19]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[OH:20])=[CH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:19](=[O:20])[C:17]([C:11]1[CH:12]=[CH:13][C:14]([CH3:1])=[CH:15][CH:16]=1)=[CH2:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13749941alpha-(1-Phenylethenyl)-2,4-dichlorobenzenemethanol

Product 1

HCID 54403033HCID 54403033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To oxalyl chloride (1.01 g) in dichloromethane (10 ml) at -70° C. was added dimethylsulphoxide (1.23 g) in dichloromethane (6 ml). To the resulting mixture was dropwise added a solution of α-(1-phenylethenyl)-2,4-dichlorobenzenemethanol (2.07 g) in dichloromethane (6 ml). Triethylamine (2.17 g) was added to the reaction mixture and the resulting mixture was stirred for an additional 20 minutes and then allowed to warm to room temperature. The reaction mixture was washed with water and the organic phase separated and concentrated under reduced pressure. The resulting residue was redissolved in ethyl acetate, washed with water, dried over anhydrous magnesium sulphate. The solvent removed under reduced pressure to yield 1-(2,4-dichlorophenyl)-2-(4-methylphenyl)propen-1-one (δ (CDCl3), 5.92 (1H,s) 6.16 (1H,s) and 7.1-7.3 (10H,m) p.p.m.) as an oil having the formula: ##STR19##

Workup

  1. washThe reaction mixture was washed with water
  2. customthe organic phase separated
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was redissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customThe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-add2b7f05aff436a9d199760ba233572
Source dataset
uspto-grants-1986_12
Patent number
US04628104

Reaction notes

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