Acetone → HCID 13046229, compound

HRID 1759462Notes

Reaction equation

HRID 1759462 reaction equation
[CH3:1][C:2](=[CH:4][CH3:5])[CH3:3].[OH2:6].[OH2:7].[C:8]1(C)[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.C[C:20](C)=[O:21]>>[CH3:20][O:21][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:8]=1)[O:6][CH2:5]/[CH:4]=[C:2](\[CH3:3])/[CH:1]=[O:7]

Participants

5

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 105532-Methyl-2-buteneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 13046229HCID 13046229, compound

Procedure

A solution of 12.3 g (E)-1,1-diethoxy-4-m-methoxyphenoxy)-2-methyl-2-butene is dissolved in 125 ml acetone and treated with 25 ml water and 2.5 g p-toluenesulfonic acid monohydrate and stirred under nitrogen for 2 hours. The solution is concentrated at room temperature and the two-phase residue extracted with 100 ml benzene. The benzene extract is washed with 25 ml of 10% aqueous potassium carbonate followed by 25 ml water, dried with sodium sulfate and concentrated to yield 0.5 g orange oil which is chromatographed on a Waters LC/500 HPLC using a 500 gm silica column using 10% diethylether-hexane. Recrystallization of the product fraction from hexane containing a small portion of diethylether yields 0.23 g of the desired product. m.p. 45°-8° C. Elemental Analysis. Calculated for C12H14O3 : C,69.88; H,6.84. Found: C,69.51; H,6.59.

Workup

  1. concentrationThe solution is concentrated at room temperature
  2. extractionthe two-phase residue extracted with 100 ml benzene
  3. extractionThe benzene extract
  4. washis washed with 25 ml of 10% aqueous potassium carbonate
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-65d5aadbcacd408cac371b47685d6ff1
Source dataset
uspto-grants-1982_07
Patent number
US04340765

Reaction notes

Loading…