Anisole → HCID 53953369, compound

HRID 1419492Notes

Reaction equation

HRID 1419492 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:19][O:18][C:12]1[CH:17]=[CH:16][C:15]([C:4]([C:3]2[C:2]([Cl:1])=[C:10]([CH3:11])[CH:9]=[CH:8][CH:7]=2)=[O:5])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 193679402-Chloro-3-methylbenzoyl chloride

Product 1

HCID 53953369HCID 53953369, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloro-3-methylbenzoyl chloride (18.05 mmol), [prepared as described above] in dry CH2Cl2 (60 ml) was cooled to 0° C. and AICl3 (2.41 g, 1 eq.) was added. After ten minutes, anisole (1.96 ml, 1 eq.) was added. The resulting orange colored reaction mixture was allowed to warm to room temperature, stirred for 3 h and then poured on ice. The product was extracted into ether, washed with brine, and dried over MgSO4 . The solvent was evaporated in vacuo to give 3-(4-methoxybenzoyl)-2-chlorotoluene (4.55 g, 97% yield) as a solid, mp 64.7°-65.8° C.

Workup

  1. additionAICl3 (2.41 g, 1 eq.) was added
  2. waitAfter ten minutes
  3. temperatureto warm to room temperature
  4. additionpoured on ice
  5. extractionThe product was extracted into ether
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a1b2805c9a9443f9b71e39b049c4ad63
Source dataset
uspto-grants-1999_03
Patent number
US05886178

Reaction notes

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