Ethylene Glycol → HCID 68683108, compound

HRID 1171078Notes

Reaction equation

HRID 1171078 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].O.S(C1C=CC(C)=CC=1)(O)(=O)=O.C1(C)C=CC=CC=1.[F:24][C:25]1[CH:26]=[C:27]([C:32](=O)[CH2:33][CH3:34])[CH:28]=[C:29]([F:31])[CH:30]=1>C(OCC)(=O)C>[F:24][C:25]1[CH:26]=[C:27]([C:32]2([CH2:33][CH3:34])[O:4][CH2:1][CH2:2][O:3]2)[CH:28]=[C:29]([F:31])[CH:30]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 1456203,5-DifluoropropiophenoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 68683108HCID 68683108, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethylene glycol (773 mg) and a catalytic amount of tosylic acid monohydrate were added to a toluene (20 ml) solution of 1-(3,5-difluorophenyl)propan-1-one (1.06 g). A Dean-Stark tube was attached to the reactor, the reaction liquid was stirred overnight with heating under reflux, then diluted with ethyl acetate, and washed with aqueous saturated sodium hydrogencarbonate solution. The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated off, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain the entitled compound (1.31 g) as a colorless oil.

Workup

  1. customthe reaction liquid
  2. temperaturewith heating
  3. temperatureunder reflux
  4. washwashed with aqueous saturated sodium hydrogencarbonate solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated off
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-5b0085f2a3e14012a357edb48fa2e3c0
Source dataset
uspto-grants-2010_11
Patent number
US07829586B2

Reaction notes

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