Hydrochloric Acid → HCID 69823190, compound

HRID 432545

Reaction equation

HRID 432545 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C=C([CH2:28][CH2:29][C:30](Cl)=[O:31])C=CC=1.[Al+3].[Cl-:34].[Cl-].[Cl-].Cl>C(=S)=S>[Si:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:30](=[O:31])[CH2:29][CH2:28][Cl:34])=[CH:17][CH:18]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 149601603-Chlorobenzenepropanoyl chlorideHCID 69823535tert-Butyl(dimethyl)[(6-phenylhexyl)oxy]silane

Product 1

HCID 69823190HCID 69823190, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
-78 °C

Procedure

tert-Butyl(dimethyl)[(6-phenylhexyl)oxy]silane (21.00 g), 3-chlorophenylpropionyl chloride (9.14 g) and CS2 solvent (100 mL) were placed in a two neck flask equipped with a reflux condenser. The mixture was then cooled to −78° C. and AlCl3 (19.20 g) was added. The reaction mixture was stirred at −78° C. for 15 min., followed by: 0° C. for 20 min., 25° C. for 30 min., 40° C. for 40 min., 25° C. for 14 h. During the course of the temperature ramping, gas evolution (presumably HCl) was noted. The reaction was then quenched with several portions of 100 mL water/30 mL conc. HCl and the resulting mixture was transferred to a separatory funnel. The organic products were extracted into chloroform (4×200 mL). The chloroform fractions were combined and dried over MgSO4. The solvent was then removed by roto-evaporation to give a tan oil which solidified on standing overnight. 1H NMR shows the presence of resonances consistent with the desired product.

Workup

  1. customequipped with a reflux condenser
  2. custom0° C.
  3. customfor 20 min.
  4. wait25° C. for 30 min.
  5. wait40° C. for 40 min.
  6. wait25° C. for 14 h
  7. customThe reaction was then quenched with several portions of 100 mL water/30 mL conc. HCl
  8. customthe resulting mixture was transferred to a separatory funnel
  9. extractionThe organic products were extracted into chloroform (4×200 mL)
  10. dry with materialdried over MgSO4
  11. customThe solvent was then removed by roto-evaporation
  12. customto give a tan oil which
  13. waiton standing overnight

Sources & evidence

ORD record
ord-73ae860ca0284002ada12a421359b83a
Source dataset
uspto-grants-2003_12
Patent number
US06664111B2

Linked notes

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