Acetyl chloride → 3'-Acetyl-5-ethyl-4'-hydroxy-2-methoxybiphenyl

HRID 344926Notes

Reaction equation

HRID 344926 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]([C:11]1[CH:12]=[CH:13][C:14]([O:25][CH3:26])=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)[CH:16]=1)[CH3:10]>ClCCCl>[C:5]([C:21]1[CH:22]=[C:17]([C:15]2[CH:16]=[C:11]([CH2:9][CH3:10])[CH:12]=[CH:13][C:14]=2[O:25][CH3:26])[CH:18]=[CH:19][C:20]=1[OH:23])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 541842175-Ethyl-2,4'-dimethoxybiphenyl

Product 1

HCID 541668163'-Acetyl-5-ethyl-4'-hydroxy-2-methoxybiphenyl

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture was prepared by suspending 5.0 g of aluminium chloride into 25 ml of 1,2-dichloroethane. The mixture was added 1.0 ml of acetylchloride, stirred for 1 hour at room temperature. The reaction mixture, wherein 2.4 g of 5-ethyl-2,4'-dimethoxybiphenyl was added, was stirred for 2 hours with cooling by the ice bath and stirred from further 2 hours at room temperature. Ice water was added into the reaction mixture, and extracted with chloroform. The extract was washed with 10% water solution of sodium hydrogencarbonate and an aqueous solution saturated with NaCl, dried with sodium sulfate and concentrated. The concentrate was purified by a silica gel column-chromatography (n-hexane:ethyl acetate=50:1) to yield 1.6 g of 3'-acetyl-5-ethyl-4'-hydroxy-2-methoxybiphenyl.

Workup

  1. customA mixture was prepared
  2. stirringwas stirred for 2 hours
  3. stirringstirred from further 2 hours at room temperature
  4. extractionextracted with chloroform
  5. washThe extract was washed with 10% water solution of sodium hydrogencarbonate
  6. dry with materialan aqueous solution saturated with NaCl, dried with sodium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by a silica gel column-chromatography (n-hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-d1513cbbb65d42759e59fa8ab6c55737
Source dataset
uspto-grants-1991_10
Patent number
US05053548

Reaction notes

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