4-Hydroxybenzophenone → {4-[(2,2-Dimethyl-1,3-dioxan-5-yl)methoxy]phenyl}(phenyl)methanone

HRID 931687Notes

Reaction equation

HRID 931687 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:23][CH:24]1[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[O:26][CH2:25]1)(=O)=O.OCC(CO)CO>CN(C)C=O.O>[CH3:30][C:27]1([CH3:31])[O:28][CH2:29][CH:24]([CH2:23][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:7])=[CH:14][CH:15]=2)[CH2:25][O:26]1

Participants

7

Reactant 4

HCID 143474-HydroxybenzophenoneHCID 24758Sodium hydrideHCID 78432TrimethylolmethaneHCID 10998661(2,2-Dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate

Product 1

HCID 89907866{4-[(2,2-Dimethyl-1,3-dioxan-5-yl)methoxy]phenyl}(phenyl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzophenone is treated with equimolar quantity of sodium hydride in dry dimethylformamide at 0° C. under an inert atmosphere. After stirring at ambient temperature for 2 hours, a bright yellow clear solution is obtained. To this solution is added equimolar quantity of (2,2-dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate (its synthesis in two steps from commercially available 2-hydroxymethyl-1,3-propanediol is described in European Patent EP2103611). After stirring at ambient temperature for 16 hours, the reaction mixture is diluted with water and extracted with dichloromethane. The organic phase is evaporated to dryness and the crude product is purified by column chromatography. This provide the intermediate {4-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]phenyl}(phenyl)methanone. This intermediate is then dissolved in acetone, excess of 1M hydrochloric acid is added and the reaction mixture is stirred for 2 hours at room temperature. The reaction mixture is evaporated to dryness under reduced pressure, and the residue is purified by column chromatography to provide the desired {4-[3-hydroxy-2-(hydroxymethyl)propoxy]phenyl}(phenyl)methanone.

Workup

  1. customa bright yellow clear solution is obtained
  2. stirringAfter stirring at ambient temperature for 16 hours
  3. extractionextracted with dichloromethane
  4. customThe organic phase is evaporated to dryness
  5. customthe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-5aa3a378cda948f6a4553f6115b9d042
Source dataset
uspto-grants-2016_03
Patent number
US09296835B2

Reaction notes

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