Ammonium Chloride → HCID 11276762, compound

HRID 2267995Notes

Reaction equation

HRID 2267995 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][CH2:4][S:5][C:6]1[C:7]([CH3:16])=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].[Cl-].[NH4+]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[C:15]2[C:6](=[C:7]([CH3:16])[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=2)[S:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 11414044HCID 11414044, compound

Product 1

HCID 11276762HCID 11276762, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

67.9 g (0.27 mol) of methyl 3-(3-methyl-2-butenylthio)-2-methylbenzoate were dissolved in 600 ml of methylene chloride and, at −5 to 0° C., 206.4 g (1.09 mol) of titanium tetrachloride in 600 ml of methylene chloride were added dropwise, and the mixture was stirred at 0° C. for three hours. The mixture was subsequently stirred into 1.5 kg of ice and 500 ml of saturated ammonium chloride solution, the organic phase was separated off and dried and the solvent was removed. This gave 62.9 g of an orange oil which was directly used further. To characterize the product, a sample was chromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=10/1).

Workup

  1. customthe organic phase was separated off
  2. customdried
  3. customthe solvent was removed
  4. customa sample was chromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-6f435fb3d876427e95a848dcf81e3797
Source dataset
uspto-grants-2001_12
Patent number
US06326333B1

Reaction notes

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