Acetone → HCID 10048016, compound

HRID 482134Notes

Reaction equation

HRID 482134 reaction equation
[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:21](=[O:24])([O-])[O-].[K+].[K+].C[C:28]([CH3:30])=[O:29]>>[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:2][CH2:1][O:13][CH2:14][CH2:15][O:29][CH2:28][CH2:30][O:24][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 9993719HCID 9993719, compound

Product 1

HCID 10048016HCID 10048016, compoundYield 74%

Procedure

A mixture of 2-dodecyloxyphenol (4.75 g, 17.1 mmole), 3,6,9-trioxadecyl-p-toluene sulphonate24 (6 g, 18.9 mmole), dry acetone (50 ml) and anhydrous potassium carbonate (2.6 g, 18.9 mmole) was stirred and heated to reflux under a nitrogen atmosphere for 48 h. Upon cooling the reaction mixture was filtered and the acetone removed under reduced pressure. Distillation of the resultant oil, under reduced pressure, gave 1-dodecyloxy-2-(1,4,7,10-tetraoxaundecyl)benzene as a clear oil (5.4 g, 74%), b.p. 245° C./0.4 mmHg; MS (CI) m/e 442 (M+ +NH4+), δH (200 MHz, CDCl3) 0.88(t, 3H), 1.26(br s, 18H), 1.80(q, 2H), 3.38 (s, 3H), 3.50-3.80 (m, 8H), 3.87 (t, 2H), 3.98 (t, 2H), 4.17(t, 2H) and 6.90(s, 4H) which was used in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux under a nitrogen atmosphere for 48 h
  3. temperatureUpon cooling the reaction mixture
  4. filtrationwas filtered
  5. customthe acetone removed under reduced pressure
  6. distillationDistillation of the resultant oil

Sources & evidence

ORD record
ord-7065c2765d8a44fcbdf8f6499f76886c
Source dataset
uspto-grants-1998_08
Patent number
US05792860

Reaction notes

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