Mesitylene → 5-(2,4,6-Trimethylbenzyl)furan-2-carboxylic acid methyl ester

HRID 1814698Notes

Reaction equation

HRID 1814698 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.Cl[CH2:11][C:12]1[O:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[CH3:20][O:19][C:17]([C:15]1[O:16][C:12]([CH2:11][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[CH:13][CH:14]=1)=[O:18]

Participants

5

Reactant 3

HCID 7947MesityleneHCID 75065Methyl 5-(chloromethyl)-2-furoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 537173175-(2,4,6-Trimethylbenzyl)furan-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3,5-Trimethylbenzene (6.85 g, 57 mmol), methyl 5-chloromethyl-2-furanoate (2.48 g, 14.2 mmol) and aluminum trichloride (2.46 g, 18 mmol) were refluxed in dichloromethane (30 mL) for 4 h. The reaction was quenched with water, and the two layers were separated. The organic layer was concentrated and passed through a silica gel column. Hexane was used as the mobile phase to elute the product. The 5-(2,4,6-trimethylbenzyl)furan-2-carboxylic acid methyl ester was obtained as a yellow oil (86%).

Workup

  1. customThe reaction was quenched with water
  2. customthe two layers were separated
  3. concentrationThe organic layer was concentrated
  4. washto elute the product

Sources & evidence

ORD record
ord-7ae27cf456b24f4bb6f15e39aca75976
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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