Dimethyl Sulfoxide → Benzene, 1-((2-(3,4-dichlorophenyl)-2-methylpropoxy)methyl)-3-(4-methoxyphenoxy)-

HRID 1589449Notes

Reaction equation

HRID 1589449 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:13])([CH3:12])[CH2:10]Cl)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:14][O:15][C:16]1[CH:30]=[CH:29][C:19]([O:20][CH:21](O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24]C=2)=[CH:18][CH:17]=1.[OH-:31].[Na+].[CH3:33]S(C)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:13])([CH3:12])[CH2:10][O:31][CH2:33][C:25]2[CH:26]=[CH:27][CH:22]=[C:21]([O:20][C:19]3[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:30][CH:29]=3)[CH:24]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium Hydroxide2×HCID 20247090HCID 20247090, compoundHCID 53836187HCID 53836187, compound

Product 1

HCID 3067147Benzene, 1-((2-(3,4-dichlorophenyl)-2-methylpropoxy)methyl)-3-(4-methoxyphenoxy)-Yield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 9.98 g of 2-(3,4-dichlorophenyl)-2-methylpropyl chloride, 9.67 g of 4-methoxyphenoxybenzyl alcohol, 3.9 g of 45% sodium hydroxide and 48 g of dimethylsulfoxide was heated and stirred at 140° C. for 3 hours, and 1.8 g of 45% sodium hydroxide was further added, and the reaction was kept at the same temperature for 4 hours, poured into water, and was extracted with benzene. The benzene extract was washed with water, dried over Na2SO4, and evaporated under reduced pressure and the obtained crude ether was purified by column chromatography on 250 g of silica gel (1:1 mixed solvent of toluene and n-hexane was used as eluent) to give 3.34 g of the desired ether (the yield was 78% of the theoretical yield based on consumed 2-(3,4-dichlorophenyl)-2-methylpropyl chloride).

Workup

  1. temperaturewas heated
  2. waitthe reaction was kept at the same temperature for 4 hours
  3. extractionwas extracted with benzene
  4. extractionThe benzene extract
  5. washwas washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure
  8. customthe obtained crude ether
  9. customwas purified by column chromatography on 250 g of silica gel (1:1 mixed solvent of toluene and n-hexane was used as eluent)
  10. customto give 3.34 g of the desired ether (the yield was 78% of the
  11. customtheoretical yield
  12. customon consumed 2-(3,4-dichlorophenyl)-2-methylpropyl chloride)

Sources & evidence

ORD record
ord-0bee2d07b0f143d0b98bcd1a762a4a07
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

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