Water → HCID 23134229, compound

HRID 2220636Notes

Reaction equation

HRID 2220636 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=2)=[C:11]([CH3:25])[CH:10]=1.C(N(CC)CC)C.O>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH3:25])[C:12]([C:16]2[CH:17]=[CH:18][C:19]([C:22](=[O:24])[CH3:23])=[CH:20][CH:21]=2)=[C:13]([CH3:15])[CH:14]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23134219HCID 23134219, compound

Product 1

HCID 23134229HCID 23134229, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetyl chloride (0.226 mL) was added to a mixture of 1-[4′-(2-hydroxyethoxy)-2′,6′-dimethylbiphenyl-4-yl]ethan-1-one (0.75 g) and triethylamine (0.556 mL) in methylene chloride (2 mL), and the mixture was stirred at room temperature for 20 minutes. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3-1/2) to afford 1-[4′-(2-acetoxyethoxy)-2′,6′-dimethylbiphenyl-4-yl]ethan-1-one (0.672 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3-1/2)

Sources & evidence

ORD record
ord-0489cf59a4074f889b466001ea36219c
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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