Dimethyl Sulfoxide → HCID 13879178, compound

Temperature

115 °C

Using the general procedure described in Example 1 a reactor was charged with 83.7 g (0.55 mole) of methyl-p-hydroxybenzoate, 43.28 g of a 50% by weight aqueous solution of sodium hydroxide (0.54 mole NaOH), 112 cc dimethylsulfoxide and 120 cc toluene. The resultant mixture was heated to the boiling point for six hours under a nitrogen atmosphere to remove all of the water present by azeotropic distillation. The reaction mixture was then allowed to cool to about 75° C. at which time 109 g (0.56 mole) of 3-chloropropyl trimethoxysilane were added dropwise while the reaction mixture was stirred. Following completion of the addition the reaction mixture was heated at 115° C. for about 16 hours, following which the mixture was allowed to cool and was filtered to remove any sold material. The solvents were then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C. The pressure was then reduced to 2 mm of mercury and the material boiling from 230° to 235° C. was collected. The weight of this fraction was equivalent to a yield of 92% based on starting materials. Analysis by vapor phase chromatography indicated that the purity of the product was greater than 98%. The infrared and nuclear magnetic resonance spectra of the product was consistent with the proposed structure.

1. customto remove all of the water present
2. distillationby azeotropic distillation
3. additionwere added dropwise while the reaction mixture
4. additioncompletion of the addition the reaction mixture
5. temperatureto cool
6. filtrationwas filtered
7. customto remove any sold material
8. customThe solvents were then removed under a pressure of about 15 mm of mercury at a temperature of about 60° C
9. customboiling from 230° to 235° C.
10. customwas collected

ORD record

ord-bea347361cd24700be77155da900d1ad

Source dataset

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04645844