Water → Benzene, 1-((2-(4-(difluoromethoxy)phenyl)-2-methylpropoxy)methyl)-3-phenoxy-

HRID 1589447Notes

Reaction equation

HRID 1589447 reaction equation
[F:1][CH:2]([F:15])[O: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.[O:16]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+].O>[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1C=CC=CC=1>[F:1][CH:2]([F:15])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH3:13])([CH3:14])[CH2:11][O:12][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:24]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 932913-Phenoxybenzyl chlorideHCID 15582647HCID 15582647, compound

Product 1

HCID 3067125Benzene, 1-((2-(4-(difluoromethoxy)phenyl)-2-methylpropoxy)methyl)-3-phenoxy-Yield 81%

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 241BenzeneSolvent

Procedure

2.0 g of 2-(4-difluoromethoxyphenyl)-2-methylpropyl alcohol, 2.0 g of m-phenoxybenzyl chloride, 20 g of 50% NaOH and 0.3 g of triethylbenzyl ammonium bromide were stirred at 50° C. for 2 hours. Then, H2O and benzene were added to the reaction mixture, and the mixture was sufficiently shaken and the benzene layer was separated, washed with water, dried over Na2SO4, and evaporated under reduced pressure, and the obtained crude ether was purified by column chromatography on 130 g of silica gel (2:3 mixed solvent of toluene and hexane was used as eluent) to give 3.0 g of the desired ether (the yield was 81% of the theoretical yield).

Workup

  1. customthe benzene layer was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customthe obtained crude ether
  6. customwas purified by column chromatography on 130 g of silica gel (2:3 mixed solvent of toluene and hexane was used as eluent)
  7. customto give 3.0 g of the desired ether (the yield was 81% of the
  8. customtheoretical yield)

Sources & evidence

ORD record
ord-e5c87c050b8144e09b8d5904b847eb0d
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

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