4-Hydroxybenzaldehyde → 3-(4-Formylphenoxy)propyltrimethoxysilane
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CS(C)=O.[OH-].[Na+].Cl[CH2:17][CH2:18][CH2:19][Si:20]([O:25][CH3:26])([O:23][CH3:24])[O:21][CH3:22]>C1(C)C=CC=CC=1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:17][CH2:18][CH2:19][Si:20]([O:25][CH3:26])([O:23][CH3:24])[O:21][CH3:22])=[CH:3][CH:4]=1)=[O:7]Participants
Procedure
Using the general procedure described in the preceding Example 1, a reactor was charged with 62.2 g (0.55 mole) p-hydroxybenzaldehyde, 112 cc dimethylsulfoxide, 120 cc toluene and 43.2 g of a 50% aqueous sodium hydroxide solution containing 0.54 mole NaOH. All of the water present was removed by azeotropic distillation at a temperature of about 110° to 115° C. The reaction mixture was heated to the boiling point during the gradual addition of 109 g (0.55 mole) of 3-chloropropyl trimethoxysilane. The product, 3(p-formylphenoxy)propyl trimethoxysilane, was isolated by filtration and removal of the solvents from the recovered liquid phase under reduced pressure, followed by fractional distillation of the residue. The fraction boiling at 208° C. at a pressure of 3 mm of mercury was collected (85% yield, based on silane). The infrared and nuclear magnetic resonance spectra of the distillate confirm the proposed structure ##STR17## The vapor phase chromatogram of the product indicated a purity of greater than 98%.
Workup
- customAll of the water present was removed by azeotropic distillation at a temperature of about 110° to 115° C
Sources & evidence
- ORD record
- ord-19ce652934b74b5f963bda3501d19ea2
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04645844
Reaction notes
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