Hydrochloric Acid → 1-(Chloromethyl)-4-(methylthio)benzene

HRID 1359481Notes

Reaction equation

HRID 1359481 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.[ClH:11]>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 592968[4-(Methylsulfanyl)phenyl]methanol

Product 1

HCID 701281-(Chloromethyl)-4-(methylthio)benzeneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

Under an atmosphere of nitrogen, 78.7 g (500 mmo)l [sic] of 4-(methylthio)benzyl alcohol were dissolved in 154.5 g of toluene. 131.6 g, (1.3 mol) of conc. HCl were added, and the mixture was stirred at 20-25° C. for 30 min. After 2 h (no starting materialleft according to TLC), the reaction mixture was diluted with 349 g of toluene and the aqueous phase was separated off. The organic phase was neutralized using 14.0 g of NaHCO and, after 15 min, filtered, and the solvent was evaporated. The residue that remained consisted of 107.4 a of a yellow oil with toluene, corresponding to a yield of >95% (according to NMR).

Workup

  1. waitAfter 2 h (no starting materialleft according to TLC
  2. customthe aqueous phase was separated off
  3. waitafter 15 min
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f89ea8d062754c9b907a74ddc5b30666
Source dataset
uspto-grants-2003_07
Patent number
US06600046B2

Reaction notes

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