Acetone → HCID 23454196, compound

HRID 1277513Notes

Reaction equation

HRID 1277513 reaction equation
[CH:1]([C:19]1[CH:25]=[C:24](O)[CH:23]=[CH:22][C:20]=1[OH:21])([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:2].[OH-].[Na+].S([O:34][CH3:35])(OC)(=O)=O.[CH3:36]C(C)=O>>[CH3:36][O:21][C:20]1[CH:22]=[CH:23][C:24]([O:34][CH3:35])=[CH:25][C:19]=1[CH:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 13796215HCID 13796215, compound

Product 1

HCID 23454196HCID 23454196, compound

Procedure

Alternatively, the above 2-sec-octadecylhydroquinone dimethyl ether was also obtained by the etherification of 2-sec-octadecylhydroquinone. Thus, 5.0 g of 2-sec-octadecylhydroquinone were dissolved in 50 ml of acetone and 1.2 g sodium hydroxide were added. After the dropwise addition of 3.8 g of dimethyl sulfate at room temperature, the reaction mixture was refluxed for 2 hours. The solvent was distilled off under reduced pressure and the residue was extracted with ether. After being washed with water and dried, the residue was distilled under reduced pressure to give 2.0 g of 2-sec-octadecylhydroquinone dimethyl ether having b.p. 200°-206° C./0.6 mmHg. IR and NMR data of both products were completely identical.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionthe residue was extracted with ether
  4. washAfter being washed with water
  5. customdried
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-eee1a16f7e214685a0b070160cdaed18
Source dataset
uspto-grants-1981_07
Patent number
US04277553

Reaction notes

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