Water → HCID 13535664, compound

HRID 1583591Notes

Reaction equation

HRID 1583591 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([O:6][CH2:7]Cl)=[CH:4][CH:3]=1.[F:11][CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1.[OH-].[Na+].O>[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([O:6][CH2:7][O:20][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][F:11])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 88801alpha,4-DichloroanisoleHCID 13367643(4-(2-Fluoroethoxy)phenyl)methanol

Product 1

HCID 13535664HCID 13535664, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture composed of 1.0 g of 4-chlorophenoxychloromethane, 1.0 g of 4-(2-fluoroethoxy)benzyl alcohol, 0.3 g of triethylbenzylammonium bromide and 20 g of a 50% aqueous solution of sodium hydroxide was stirred at 50° C. for 1.5 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. The resulting crude ether was recrystallized from benzene to give 1.18 g of the desired 4-(2-fluoroethoxy)benzyl 4-chlorophenoxymethyl 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
  7. customThe resulting crude ether was recrystallized from benzene

Sources & evidence

ORD record
ord-064e35db6f1f43bbb7d1bef02a8794f8
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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