Ethylene Glycol → HCID 59323310, compound

HRID 2390067Notes

Reaction equation

HRID 2390067 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[CH:3]=1.[CH2:13](O)[CH2:14][OH:15].COC(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:9]([CH3:10])[CH3:11])[O:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 203973111-(3-Bromophenyl)-2-methylpropan-1-one

Product 1

HCID 59323310HCID 59323310, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

150 mg of 1-bromo-3-isobutyrylbenzene, 204 mg of ethylene glycol, 350 mg of trimethylorthoformate, and 10 mg of p-toluene sulfonic acid were dissolved in 4 mL of toluene, followed by stirring at 60° C. for 2 days. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 146 mg (yield 80%) of a title compound as a pale yellow oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was then washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce6d8296cd0b47f6af2f8c2664c32eb9
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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