Isobutylene → HCID 54448092, compound

HRID 361969Notes

Reaction equation

HRID 361969 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([OH:12])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[CH3:15])=[O:5].FC(F)(F)S(O)(=O)=O.[CH3:29][C:30]([CH3:32])=[CH2:31].[OH-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([O:12][C:30]([CH3:32])([CH3:31])[CH3:29])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[CH3:15])=[O:5]

Participants

7

Reactant 4

HCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 53938437HCID 53938437, compound

Product 1

HCID 54448092HCID 54448092, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 2,6-dichloro-5'-hydroxy-4'-methoxy-2'-methyl-benzophenone (3.0 g; 9.6 mmol) in 50 ml of methylenechloride is cooled down to -70° C., trifluoromethanesulfonic acid (0.3 ml) is added, then a stream of 2-methylpropene (5.5 g; 100 mmol) is introduced within 4 hours. Triethylamine (1.2 ml) is added, the temperature goes up to 20° C. The solution is shaken twice with diluted sodium hydroxide and the solventis evaporated. The residue is purified chromatographically (flash column with 30 g of silicagel, elution with toluene/acetone 20:1 (v/v)). The residue is treated with petrolether to give 0.7 g of white crystals (20% y); mp. 102° C.

Workup

  1. customgoes up to 20° C
  2. customthe solventis evaporated
  3. customThe residue is purified chromatographically
  4. wash(flash column with 30 g of silicagel, elution with toluene/acetone 20:1 (v/v))
  5. additionThe residue is treated with petrolether

Sources & evidence

ORD record
ord-6d06a1029808430989d31e83271fe97d
Source dataset
uspto-grants-1999_02
Patent number
US05866722

Reaction notes

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