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

HRID 1589450Notes

Reaction equation

HRID 1589450 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:28])([CH3:27])[CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)=[CH:6][CH:5]=1.Cl[CH2:30][O:31][CH2:32][CH3:33].O>O1CCCC1>[CH2:32]([O:31][CH2:30][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH3:28])([CH3:27])[CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:15]=2)=[CH:8][CH:9]=1)[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 157700Phenol, 4-(1,1-dimethyl-2-((3-phenoxyphenyl)methoxy)ethyl)-

Product 1

HCID 3067186Benzene, 1-((2-(4-(ethoxymethoxy)phenyl)-2-methylpropoxy)methyl)-3-phenoxy-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 50 ml dry tetrahydrofuran was added 1.0 g of sodium hydride (60% in oil) and then 5.0 g of 3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether in 15 ml of dry tetrahydrofuran was added dropwise to the mixture under reflux over a period of 30 minutes. The mixture was further refluxed for 10 minutes and 5.0 ml of ethyl chloromethyl ether was added dropwise to the mixture for 30 minutes. And the resulting mixture was further refluxed for 10 minutes, cooled to room temperature, poured into water, and extracted with benzene. The benzene extract was washed with water, dried over Na2SO4, and evaporated to give the oily residue which was purified by column chromatography on 150 g silica gel (20:1 mixed solvent of benzene and ether was used as eluent) to give 5.0 g of 3-phenoxybenzyl 2-(4-ethoxymethoxyphenyl)-2-methylpropyl ether.

Workup

  1. temperatureunder reflux over a period of 30 minutes
  2. temperatureThe mixture was further refluxed for 10 minutes
  3. temperatureAnd the resulting mixture was further refluxed for 10 minutes
  4. extractionextracted with benzene
  5. extractionThe benzene extract
  6. washwas washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customto give the oily residue which
  10. customwas purified by column chromatography on 150 g silica gel (20:1 mixed solvent of benzene and ether was used as eluent)

Sources & evidence

ORD record
ord-65a3c4db48a44ad1b0e81d98dd4b75f7
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

Loading…