Toluene → HCID 131717886, compound

HRID 1591237Notes

Reaction equation

HRID 1591237 reaction equation
C1(C)C=CC=CC=1.C(C1C=CC=CC=1O)C=C.C[SiH](C)O[SiH](C)C.[OH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH2:33][CH2:34][Si:35]([CH3:51])([CH3:50])[O:36][Si:37](CCCC1C=CC=CC=1O)([CH3:39])[CH3:38]>C(O)(CC)(C)C>[OH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH2:33][CH2:34][Si:35]([CH3:51])([CH3:50])[O:36][SiH:37]([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 156242-AllylphenolHCID 186591,1,3,3-Tetramethyl-disiloxaneHCID 22111943HCID 22111943, compound

Product 1

HCID 131717886HCID 131717886, compound

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
85 °C

Procedure

To a 85 ml toluene solution containing 67.1 g (0.5 mole) of 2-allylphenol and 0.4 g of a 5% solution of H2PtCl6 in t-amyl alcohol is added a solution consisting of 15 ml of toluene and 38.8 g (0.25 mole) of 1,1,3,3-tetramethyldisiloxane at 75° C. The addition is complete in 1 hour. The mixture is heated at 85° C. for 1 hour and then at 105° C. for 3 hours. After washing successively three times with 100 ml portions of water, 101 g of the 2:1 molar adduct, 1,3-bis-(3-(2-hydroxylphenyl)-propyl)-1,1,3,3-tetramethyldisiloxane (>92% pure by gel chromatography, GC) having a light straw color is obtained after stripping off solvent. The structure of the product 1,3-bis-(3-(2-hydroxylphenyl)-propyl)-1,1,3,3-tetramethyldisiloxane is confirmed by 1H NMR and IR (neat).

Workup

  1. additionis added a solution
  2. additionThe addition
  3. waitat 105° C. for 3 hours
  4. washAfter washing successively three times with 100 ml portions of water, 101 g of the 2
  5. customis obtained

Sources & evidence

ORD record
ord-b30a697ee6274ca699ce791e39d6e1dd
Source dataset
uspto-grants-1993_04
Patent number
US05206312

Reaction notes

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