Hydrochloric Acid → 2-Dimethylvinylsiloxy-tricyclo[3.3.1.13,7]decane

HRID 1351761Notes

Reaction equation

HRID 1351761 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[OH:11])[CH2:8]2.C(N(CC)CC)C.Cl[SiH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].Cl>C1(C)C=CC=CC=1>[CH3:23][C:22]([CH3:24])=[CH:21][SiH2:20][O:11][CH:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 641492-AdamantanolHCID 57370515C4H9ClSi

Product 1

HCID 1317264462-Dimethylvinylsiloxy-tricyclo[3.3.1.13,7]decane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Tricyclo[3.3.1.13,7]decanol (25 g), triethylamine (28 g) and toluene (250 g) were charged in a four-necked 500 ml flask, and then chlorodimethylvinylsilane (30 g) was dropwise added to the mixture at 40° C. over one hour while well stirring. The mixture was stirred at 40° C. for 7 hours with monitoring the progress of the reaction by gas chromatography. After the completion of the reaction, a 4% hydrochloric acid (300 ml) was added to the reaction mixture, and then the mixture was separated. The organic layer was washed with water and concentrated by evaporating off toluene contained in the organic layer, and the residue was distilled under reduced pressure to obtain 2-dimethylvinylsiloxy-tricyclo[3.3.1.13,7]decane having the following structure (40 g):

Workup

  1. stirringThe mixture was stirred at 40° C. for 7 hours
  2. customthe progress of the reaction by gas chromatography
  3. customAfter the completion of the reaction
  4. customthe mixture was separated
  5. washThe organic layer was washed with water
  6. concentrationconcentrated
  7. customby evaporating off toluene
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-9ac8ad52a7cb4a3bb8b38f05411447b9
Source dataset
uspto-grants-2007_05
Patent number
US07217830B2

Reaction notes

Loading…