2-Tert-Butylphenol → 7-(1,1-Dimethylethyl)-2,3-benzofurandione

HRID 2165095Notes

Reaction equation

HRID 2165095 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:12](Cl)(=[O:16])[C:13](Cl)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C1C=CN=CC=1.ClCCl.O.C(Cl)(Cl)Cl>[CH3:3][C:1]([C:5]1[C:6]2[O:11][C:13](=[O:14])[C:12](=[O:16])[C:7]=2[CH:8]=[CH:9][CH:10]=1)([CH3:4])[CH3:2]

Participants

8

Reactant 3

HCID 69232-Tert-ButylphenolHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 122942517-(1,1-Dimethylethyl)-2,3-benzofurandioneYield 47,987%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-tert-butylphenol (15 g, 0.1 mmol) and 4-dimethylaminopyridine (0.5 g) is stirred under nitrogen in 300 ml of dichloromethane. Oxalyl chloride (20 ml, 0.22 moles) is added dropwise, then the mixture is heated to reflux. After ten hours the mixture is cooled and the solvent is removed under reduced pressure. The residue is taken up in 100 ml of 1,2-dichloroethane and added dropwise under nitrogen to a suspension of aluminum chloride (40 g, 0.3 mmol) in 300 ml of 1,2-chloroethane. After 20 hours at room temperature the mixture is slowly diluted with water until all solids dissolve. The organic layer is separated and dried over molecular sieves, and the solvent is evaporated to leave a syrup which is taken up in chloroform and filtered through a short column of silica gel. The filtrate is stripped of solvent under reduced pressure to leave the product (9.8 g) as a syrup suitably pure for subsequent reactions.

Workup

  1. temperaturethe mixture is heated to reflux
  2. temperatureAfter ten hours the mixture is cooled
  3. customthe solvent is removed under reduced pressure
  4. dissolutiondissolve
  5. customThe organic layer is separated
  6. customdried over molecular sieves
  7. customthe solvent is evaporated
  8. customto leave a syrup which
  9. filtrationfiltered through a short column of silica gel

Sources & evidence

ORD record
ord-7689778f11974050aeef94ec9a88b325
Source dataset
uspto-grants-1990_07
Patent number
US04939133

Reaction notes

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