Carbon Tetrachloride → 2-Methyl-5-phenylbenzyl chloride

HRID 1883639Notes

Reaction equation

HRID 1883639 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:36]>>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4][Cl:36]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 12056528(4-Methylbiphenyl-3-yl)methanol

Product 1

HCID 235082292-Methyl-5-phenylbenzyl chloride

Procedure

500 mg (2.52 mmol) of 2-methyl-5-phenylbenzyl alcohol (produced in the same manner as in Reference Production Example 1 (4)) was dissolved in 2 ml of carbon tetrachloride, and to this solution was added 1.0 g (3.28 mmol) of triphenylphosphine under nitrogen atmosphere. The reaction mixture was stirred for 1.5 hours under reflux with heating, cooled to room temperature, then, concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=10/1 (v/v)), to obtain 508 mg of 2-methyl-5-phenylbenzyl chloride.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a2993cb00ac24ccaa4d4efdfa25b68a4
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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