Chloroacetyl chloride → 2-Chloroacetyl-4-(5-ethyl-2-methoxyphenyl)phenol

HRID 344932Notes

Reaction equation

HRID 344932 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[CH2:10]([C:12]1[CH:13]=[CH:14][C:15]([O:26][CH3:27])=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)[CH:17]=1)[CH3:11]>ClCCCl>[Cl:5][CH2:6][C:7]([C:20]1[CH:19]=[C:18]([C:16]2[CH:17]=[C:12]([CH2:10][CH3:11])[CH:13]=[CH:14][C:15]=2[O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[OH:24])=[O:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 541842175-Ethyl-2,4'-dimethoxybiphenyl

Product 1

HCID 544553712-Chloroacetyl-4-(5-ethyl-2-methoxyphenyl)phenol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture was prepared by suspending 25 g of aluminium chloride into 100 ml of 1,2-dichloroethane. The mixture, wherein 5 ml chloroacetyl chloride was added, was stirred for 1 hour at room temperature, followed by dropwise addition of 5-ethyl-2,4'-dimethoxy-biphenyl, wherein 10 g of 1.2-dichloroethane was dropwise and stirred overnight at room temperature. The reaction mixture was transferred into ice water to extract with dichloroethane. The extract was washed with saturated salt water, dried with sodium sulfate and concentrated. The concentrate was purified by a silica gel column chromatography (10:1, n-hexane:ethyl acetate) and recrystallized from chloroform/n-hexane to yield 2.5 g of light yellow and powdered 2-chloroacetyl-4-(5-ethyl-2-methoxyphenyl)phenol having a m.p. of 67.0°-68.0° C. Then, the fraction which was eluted with n-hexane/ethyl acetate: 3/1, was concentrated. The concentrate was recrystallized from chloroform/n-hexane to yield 1.5 g of white powder 3,3-bischloroacetyl-5-ethyl-2,4'-biphenyldiol having a m.p. of 154.0°-155.5° C.

Workup

  1. customA mixture was prepared
  2. stirringstirred overnight at room temperature
  3. extractionto extract with dichloroethane
  4. washThe extract was washed with saturated salt water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by a silica gel column chromatography (10:1, n-hexane:ethyl acetate)
  8. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-c1350cb312864b1f8bb82d3a38d06fab
Source dataset
uspto-grants-1991_10
Patent number
US05053548

Reaction notes

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