Methanol → HCID 21274166, compound

HRID 1383219

Reaction equation

HRID 1383219 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:15]2[CH2:17][CH2:16]2)=[C:9]2SCCCS2)=[CH:4][CH:3]=1.[OH2:18].[CH3:19][OH:20]>C(OCC)C.[Hg](Cl)Cl>[CH:15]1([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]([O:20][CH3:19])=[O:18])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 539201222-[(4-Chlorophenyl)cyclopropylmethylene]-1,3-dithiane

Product 1

HCID 21274166HCID 21274166, compound

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10.0 grams (0.036 mole) of 2-[(4chlorophenyl)cyclopropylmethylene]-1,3-dithiane, 24.0 grams (0.086 mole) of mercury (II) chloride, and 5 mL of water in 50 mL of methanol was stirred at ambient temperature for 18 hours. The reaction mixture was heated at reflux for one hour, cooled, and then was diluted with diethyl ether. The mixture was filtered through diatomaceous earth and then was dried with magnesium sulfate. The mixture was filtered through silica gel, and the filtrate was concentrated under reduced pressure, yielding 5.9 grams of methyl 2-cyclopropyl-2-(4-chlorophenyl)acetate as an oil. The nmr spectrum was consistent with the proposed structure. The reaction was run again to produce an additional 7.1 grams of the acetate.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for one hour
  3. temperaturecooled
  4. filtrationThe mixture was filtered through diatomaceous earth
  5. dry with materialwas dried with magnesium sulfate
  6. filtrationThe mixture was filtered through silica gel
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bed9866317c6414aa5b19fd0e979cfd9
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Linked notes

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