Water → HCID 13367596, compound

HRID 1583587Notes

Reaction equation

HRID 1583587 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8]Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=[CH:16][CH:15]=1.[OH-].[Na+].O>[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH3:24])([CH3:23])[CH2:21][O:22][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:5]([O:4][CH2:3][CH2:2][F:1])[CH:6]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 130345572-(4-Chlorophenyl)-2-methylpropanolHCID 135356311-(Chloromethyl)-3-(2-fluoroethoxy)benzene

Product 1

HCID 13367596HCID 13367596, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture consisting of 2.0 g of 3-(2-fluoroethoxy)benzyl chloride, 2.3 g of 2-(4-chlorophenyl)-2-methylpropyl alcohol, 0.5 g of triethylbenzylammonium bromide and 5 g of a 50% aqueous solution of sodium hydroxide was stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, and poured into water. Toluene was added, and the mixture was fully stirred. The toluene layer was separated, washed with water and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (100 g) column chromatography (developing solvent: toluene) to give 2.9 g of the desired 3-(2-fluoroethoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was fully stirred
  3. customThe toluene layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customToluene was evaporated under reduced pressure
  7. customThe resulting crude ether was purified by silica gel (100 g) column chromatography (developing solvent: toluene)

Sources & evidence

ORD record
ord-e1c85974654444868703021f7b53b3c6
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

Loading…