1,2-Dichloroethane → 1,1'-(9,10-Dihydrophenanthrene-2,7-diyl)bis(2-chloroethanone)

HRID 337390Notes

Reaction equation

HRID 337390 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3].[CH:10]1[C:23]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1.C[OH:25].[Cl:26][CH2:27][CH2:28]Cl>O>[CH:10]1[C:23]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:28](=[O:25])[CH2:27][Cl:26])[CH:19]=3)[C:14]=2[CH:13]=[CH:12][C:11]=1[C:3](=[O:4])[CH2:2][Cl:1]

Participants

7

Reactant 5

HCID 111,2-Dichloroethane2×HCID 887MethanolHCID 6577Chloroacetyl chlorideHCID 130589,10-DihydrophenanthreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 867233271,1'-(9,10-Dihydrophenanthrene-2,7-diyl)bis(2-chloroethanone)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-chloroacetyl chloride (1.765 mL, 22.19 mmol) and aluminum trichloride (2.96 g, 22.19 mmol) in 1,2-dichloroethane (DCE) (20 mL), 9,10-dihydrophenanthrene (1 g, 5.55 mmol) in 1,2-dichloroethane (DCE) (20 mL) was added dropwise over 5 min at r.t. and the reaction mixture was stirred for 1 h at r.t. and 1 h at 60° C. The reaction mixture was cooled to r.t. then added to a mixture of methanol (50 mL) and H2O (50 mL) and chilled to −5° C. The slurry was warmed to ambient, stirred for 30-60 min and the solids collected. The solids were washed well with H2O and dried at 50-60° C. to constant weight.

Workup

  1. temperatureThe reaction mixture was cooled to r.t.
  2. temperaturechilled to −5° C
  3. temperatureThe slurry was warmed to ambient,
  4. stirringstirred for 30-60 min
  5. customthe solids collected
  6. washThe solids were washed well with H2O
  7. customdried at 50-60° C. to constant weight

Sources & evidence

ORD record
ord-d02e85b7cbe54701a9913176947a03d6
Source dataset
uspto-grants-2014_11
Patent number
US08889726B2

Reaction notes

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