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4-Methylbenzyl chloride → 1-Chloro-4-[[(4-methylphenyl)methyl]thio]benzene

HRID 2231791
Notes
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Reaction equation

HRID 2231791 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1>O.[Cl-].C([N+](CC)(CC)CC)C>[CH3:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 77224-Methylbenzyl chlorideHCID 7815p-ChlorothiophenolHCID 14797Potassium Hydroxide

Product 1

HCID 130603691-Chloro-4-[[(4-methylphenyl)methyl]thio]benzene

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 962
Water
Solvent
2×

Procedure

150 g of 4-chlorothiophenol in 200 ml of water, 65 g of potassium hydroxide, 10 g of tetraethylammonium chloride and 140 g of 4-methylbenzyl chloride are initially introduced into a stirred apparatus and are heated under reflux for 4 hours. 300 ml of water are then added, and the mixture is cooled. The solid product is filtered off under suction and washed with water. After the crystals have been dried, 230 g of product of melting point 72° to 73° C. remain.

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 4 hours
  3. temperaturethe mixture is cooled
  4. filtrationThe solid product is filtered off under suction
  5. washwashed with water
  6. customAfter the crystals have been dried

Sources & evidence

ORD record
ord-2729507f7eec4b98bcb261f5f21692fd
Source dataset
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04783562

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes