2,6-Lutidine → 1-Chloro-3-triphenylmethoxyhexane

HRID 1605792Notes

Reaction equation

HRID 1605792 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([OH:8])[CH2:5][CH2:6][CH3:7].[C:9]1([C:15](Br)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C(C)=CC=CC=1C.ClC1C=CC=CC=1>O>[Cl:1][CH2:2][CH2:3][CH:4]([O:8][C:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 7964ChlorobenzeneHCID 11692BromotriphenylmethaneHCID 189210071-Chlorohexan-3-ol

Product 1

HCID 203810131-Chloro-3-triphenylmethoxyhexane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 27.3 g. (0.20 moles) of 1-chloro-3-hexanol, 77.6 g. (0.24 moles) of triphenylmethyl bromide, 30.0 g. (0.28 moles of 2,6-lutidine, and 200 ml. of chlorobenzene is heated at 95°C. for 1 hour. The cooled mixture is treated with water, and the organic phase is washed successively with water and saturated sodium chloride solution. The solution is dried over magnesium sulfate and concentrated. Column chromatography of the residue on Florisil affords the subject compound as an oil, λ max. 1600, 1030, and 705 cm-1 (triphenylmethoxy group).

Workup

  1. washthe organic phase is washed successively with water and saturated sodium chloride solution
  2. dry with materialThe solution is dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-27c904114d49409889ed77e95215033e
Source dataset
uspto-grants-1976_04
Patent number
US03950406

Reaction notes

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