Dimethyl Sulfoxide → Anisole, m-pentadecyl-

HRID 2276622

Reaction equation

HRID 2276622 reaction equation
[CH2:1]([C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH3:23]S(C)=O.[OH-].[Na+].CI>O>[CH2:1]([C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 68146Hydrogenated cardanol

Product 1

HCID 578947Anisole, m-pentadecyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a two necked round bottomed flask with a reflux condenser is added 3-pentadecyl phenol, DMSO, sodium hydroxide followed by dropwise addition of alkylating agent such as methyl iodide with constant stirring at room temperature. The stirring is continued for about 6-8 hrs. The reaction mixture is then poured into deionized water and the organic matter is extracted in diethyl ether, separated the organic layer, washed with water and dried, purified to obtain 3-pentadecyl anisole.

Workup

  1. additionfollowed by dropwise addition
  2. extractionthe organic matter is extracted in diethyl ether
  3. customseparated the organic layer
  4. washwashed with water
  5. customdried
  6. custompurified

Sources & evidence

ORD record
ord-0cadd41262b44dd289521f0f2f868abf
Source dataset
uspto-grants-2015_09
Patent number
US09133089B2

Linked notes

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