p-Anisoyl chloride → HCID 89656042, compound

HRID 626205Notes

Reaction equation

HRID 626205 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:17]([C:16]2[CH:20]=[CH:21][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[O:18])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 12156Benzene, (2-chloroethoxy)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 89656042HCID 89656042, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-(2-chloroethoxy)benzene (48 g, 1.0 eq) in 400 mL CH2Cl2 at 0° C. was added dropwise a solution of 4-methoxybenzoyl chloride (62 g, 1.2 eq) and AlCl3 (49 g, 1.2 eq) in 400 mL CH2Cl2 while maintaining the temperature at 0° C. After the addition, the reaction was stirred at rt for 1 h. Then added ice water to quench the reaction and extracted with CH2Cl2. The extract was washed with brine, dried and evaporated in vacuo. Hexane (500 mL) was added to the residue, cooled to 0° C. and stirred for 30 min, then filtered and washed with cold hexane and dried to give the product as a white solid (85 g, 96%). 1H NMR (400 MHz, CDCl3) δ7.79 (dd, J=6.8 Hz, 2.0 Hz, 4H), 6.97 (dd, J=8.8 Hz, 2.0 Hz, 4H), 4.32 (t, J=6.0 Hz, 2H), 3.89 (s, 3H), 3.86 (t, J=6.0 Hz, 2H).

Workup

  1. additionAfter the addition
  2. customThen added ice water to quench
  3. customthe reaction
  4. extractionextracted with CH2Cl2
  5. washThe extract was washed with brine
  6. customdried
  7. customevaporated in vacuo
  8. additionHexane (500 mL) was added to the residue
  9. temperaturecooled to 0° C.
  10. stirringstirred for 30 min
  11. filtrationfiltered
  12. washwashed with cold hexane
  13. customdried

Sources & evidence

ORD record
ord-ffa49d17a2ab40b9856f4ee934f6a41d
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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