Water → HCID 14033039, compound

HRID 1194734Notes

Reaction equation

HRID 1194734 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([C:16]([Cl:20])=[C:17]([Cl:19])[Cl:18])[CH:15]=1)[CH2:11][OH:12].C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O>[CH3:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([C:16]([Cl:20])=[C:17]([Cl:18])[Cl:19])[CH:15]=1)[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14033038HCID 14033038, compound

Product 1

HCID 14033039HCID 14033039, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a cold (-60° C.) solution of oxalyl chloride (3.17 ml) in 65 ml of dry methylene chloride (CH2Cl2), dimethyl sulfoxide (DMSO) (5.37 ml) in 16 ml of CH2Cl2 was added followed by the addition of 7.86 g of 3-methyl-5-(trichlorovinyl)benzyl alcohol in 16 ml of CH2Cl2, to this cold mixture, triethylamine (22 ml) was slowly added. The reaction mixture was permitted to warm to room temperature over 1.5 hours. The reaction mixture was then added to 200 ml of water and the layers separated. The organic layer was repeatedly washed with water and then dried with magnesium sulfate. Concentration afforded 8.16 g of an oil which was chromatographed on silica gel (60:40 hexane:CH2Cl2 to give 7.82 g of pure aldehyde, m.p. 42°-43° C.

Workup

  1. additionwas slowly added
  2. customthe layers separated
  3. washThe organic layer was repeatedly washed with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-4366d158d3ca42afa9ddf80ff29db082
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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