Water → HCID 13535661, compound

HRID 1583590Notes

Reaction equation

HRID 1583590 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Cl)=[CH:7][CH:6]=1.[Cl:13][C:14]1[CH:25]=[CH:24][C:17]([O:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[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:25]=[CH:24][C:17]([O:18][C:19]([CH3:22])([CH3:23])[CH2:20][O:21][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][F:1])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 191086602-(4-Chlorophenoxy)-2-methylpropan-1-olHCID 202592671-(Chloromethyl)-4-(2-fluoroethoxy)benzene

Product 1

HCID 13535661HCID 13535661, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture consisting of 1.0 g of 4-(2-fluoroethoxy)benzyl chloride, 1.0 g of 2-(4-chlorophenoxy)-2-methylpropyl alcohol, 0.3 g of triethylbenzylammonium bromide and 20 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 and low-volatile components were evaporated under reduced pressure to give 1.6 g of the desired 4-(2-fluoroethoxy)benzyl 2-(4-chlorophenoxy)-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 and low-volatile components were evaporated under reduced pressure

Sources & evidence

ORD record
ord-9eefc2268fd841b5bb7506413bc17f9e
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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