2-Hydroxy-4-(3-triethoxysilylpropoxy)diphenyl ketone → 2,4-Dihydroxybenzophenone

HRID 484818Notes

Reaction equation

HRID 484818 reaction equation
C(O[Si](OCC)(OCC)CCC[O:8][C:9]1[CH:22]=[CH:21][C:12]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])=[C:11]([OH:23])[CH:10]=1)C>C(O)C.O>[OH:23][C:11]1[CH:10]=[C:9]([OH:8])[CH:22]=[CH:21][C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]

Participants

3

Reactant 1

HCID 222229302-Hydroxy-4-(3-triethoxysilylpropoxy)diphenyl ketone

Product 1

HCID 85722,4-Dihydroxybenzophenone

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 12.495 grams of recrystallized 4-allyloxy-2-hydroxybenzophenone (AHBP), 8.215 grams of triethoxysilane and 0.20 grams of the platinum substituted silica gel of Example 1 was heated at 90° C. It was found that the AHBP melted around 55° C. The reaction mixture became yellow and homogeneous. The temperature of the reaction mixture then quickly rose to 130° C. and then dropped to 90° C. After heating the mixture of an additional hour at about 90° C., the mixture was allowed to cool to 23° C., diluted with 50 ml of hexane and then filtered. The platinum substituted silica gel was recovered as a free-flowing tan powder. The filtrate was concentrated on a rotary evaporator and 20 grams of a yellow oil, a quantitative yield of product was recovered. Based on method of preparation and reverse phase TLC, 4/1;ethanol/water, the product was 4-(3'-triethoxysilylpropoxy)-2-hydroxybenzophenone (SHBP). A trace amownt of 2,4-dihydroxybenzophenone was also obtained. The 1H NMR spectrum of the SHBP was found to be identical to a spectrum of SHBP prepared from AHBP and triethoxysilane using a platinum catalyst shown by Karstedt, U.S. Pat. No. 3,775,452.

Workup

  1. customBased on method of preparation and reverse phase TLC, 4/1

Sources & evidence

ORD record
ord-2a15b473030d4b8db2218a4ebfe8c5a0
Source dataset
uspto-grants-1985_08
Patent number
US04533744

Reaction notes

Loading…