Sodium Hydroxide → Benzene, 1-((2-(4-chlorophenyl)-2-methylpropoxy)methyl)-3-(4-methylphenoxy)-

HRID 1589445Notes

Reaction equation

HRID 1589445 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])=[CH:6][CH:5]=1.[CH3:15][C:16]1[CH:30]=[CH:29][C:19]([O:20][C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH2:24]Cl)=[CH:18][CH:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][O:12][CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[C:21]([O:20][C:19]3[CH:29]=[CH:30][C:16]([CH3:15])=[CH:17][CH:18]=3)[CH:22]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 130345572-(4-Chlorophenyl)-2-methylpropanolHCID 202469851-(Chloromethyl)-3-(4-methylphenoxy)benzene

Product 1

HCID 3067126Benzene, 1-((2-(4-chlorophenyl)-2-methylpropoxy)methyl)-3-(4-methylphenoxy)-Yield 80%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 15.0 g of a 50% aqueous solution of NaOH were added 6.0 g of 2-(4-chlorophenyl)-2-methylpropyl alcohol, 8.1 g of 3-(4-methylphenoxy)benzyl chloride and 1.1 g of tetrabutyl ammonium bromide, and the mixture was stirred at 80° C. for 1 hour. The mixture was cooled to room temperature and water was added, and the mixture was extracted with toluene and the toluene extract was washed with water and 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 9.9 g of the desired ether (the yield was 80% of the theoretical yield).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with toluene
  3. extractionthe toluene extract
  4. washwas washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customthe obtained crude ether
  8. customwas purified by column chromatography on 250 g of silica gel (1:1 mixed solvent of toluene and n-hexane was used as eluent)
  9. customto give 9.9 g of the desired ether (the yield was 80% of the
  10. customtheoretical yield)

Sources & evidence

ORD record
ord-03d597e514ce48c4ab81d45effa0604a
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

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