Toluene → 2-Methyl-5-phenylbenzyl chloride

HRID 1883640Notes

Reaction equation

HRID 1883640 reaction equation
[C:1]([Cl:5])(=O)OC.[C:6]1([CH3:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH3:12][C:6]1[CH:11]=[CH:10][C:9]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:8][C:7]=1[CH2:1][Cl:5]

Participants

3

Reactant 2

HCID 1140TolueneHCID 6586Methyl chloroformate

Product 1

HCID 235082292-Methyl-5-phenylbenzyl chloride

Procedure

315 mg (1.40 mmol) of N,N-dimethyl-(2-methyl-5-phenylbenzyl)amine (produced in the same manner as in Intermediate Production Example 12) was dissolved in 3 ml of toluene, and to this solution was added 370 mg (3.92 mmol) of methyl chlorocarbonate at room temperature. Directly after addition, the reaction mixture tuned to white suspension. This while suspension was stirred at room temperature for 7 hours, then, washed with 1 N hydrochloric acid, saturated sodium bicarbonate water, and saturated saline, sequentially, and dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane, then, hexane/ethyl acetate=10/1 (v/v)), to obtain 282 mg of 2-methyl-5-phenylbenzyl chloride.

Workup

  1. additionDirectly after addition
  2. washwashed with 1 N hydrochloric acid, saturated sodium bicarbonate water, and saturated saline
  3. dry with materialsequentially, and dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07e5dc869e464a448c48c9e8793593e6
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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