Pentamethyldisiloxane → 4-(1-Pentamethyldisiloxanylhexyloxy)phenol

HRID 248568

Reaction equation

HRID 248568 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][Si](C)(C)C)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH3:19][SiH:20]([CH3:26])[O:21][Si:22]([CH3:25])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.C1([Pt](Cl)Cl)C=CC=C1>[CH3:19][Si:20]([CH3:26])([CH:1]([O:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[O:21][Si:22]([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 74037PentamethyldisiloxaneHCID 197638634-(5-Hexenyloxy)-1-trimethylsilyloxy benzene

Product 1

HCID 197638324-(1-Pentamethyldisiloxanylhexyloxy)phenolYield 94%

Reagents, catalysts & solvents 2

HCID 178479809HCID 178479809, compoundCatalystHCID 1140TolueneSolvent

Procedure

About 6.21 g (23.5 mMol) of 4-(5-hexenyloxy)-1-trimethylsilyloxy benzene, 3.48 g (23.5 mMol) of pentamethyldisiloxane and 694 mg (17.7 μMol of Pt) of 0.5 percent cyclopentadienylplatinum dichloride solution (dichloromethane) were refluxed for 7 hours in 25 ml of toluene. After the hydrosilylation was complete, the toluene was removed by vacuum distillation on a rotary evaporator. The crude product was purified by chromatography on silica gel. Further chromatography on silica gel using petroleum ether/ethyl acetate mixtures on a Harrison Research chromatotron gave 94 percent pure 4-(1-pentamethyldisiloxanylhexyloxy)phenol as a pale yellow liquid.

Workup

  1. customthe toluene was removed by vacuum distillation on a rotary evaporator
  2. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e64d83d543174ba2aecd07a474798f69
Source dataset
uspto-grants-1993_05
Patent number
US05210247

Linked notes

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