p-Toluenesulfonic acid → Methyl 4-(4-oxocyclohex-1-en-1-yl)benzoate

HRID 2356124Notes

Reaction equation

HRID 2356124 reaction equation
O1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4]CC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[O:4]=[C:5]1[CH2:10][CH2:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)=[CH:7][CH2:6]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22730331Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoate

Product 1

HCID 22730167Methyl 4-(4-oxocyclohex-1-en-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Example 420B (2.2 g) and p-toluenesulfonic acid (100 mg) in acetone (10 mL) was heated to reflux for 10 hours, filtered through a pad of silica gel (20 g), and concentrated to provide the desired product.

Workup

  1. temperatureto reflux for 10 hours
  2. filtrationfiltered through a pad of silica gel (20 g)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea9d8ce3452c44ac938fcb44d2caedcd
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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