Triethylamine → 1-Allyloxy-4-chloromethyl-benzene

HRID 33487Notes

Reaction equation

HRID 33487 reaction equation
CS([Cl:5])(=O)=O.[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][CH:11]=1)[CH:7]=[CH2:8].C(N(CC)CC)C>ClCCl>[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][Cl:5])=[CH:12][CH:11]=1)[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11744970(4-(Prop-2-en-1-yloxy)phenyl)methanol

Product 1

HCID 123479361-Allyloxy-4-chloromethyl-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.67 g (67.0 mmol) methanesulfonyl chloride were given at 0° C. to a solution of 10.0 g (60.9 mmol) (4-allyloxy-phenyl)-methanol and 9.34 ml (67.0 mmol) triethylamine in 35 ml dichloromethane and stirred at room temperature (r.t.) overnight. The mixture was poured in ice water, extracted with dichloromethane and the organic phase dried over Na2SO4. After removal of solvents the residue was purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5) to yield 3.12 g (28%) pale yellow oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialthe organic phase dried over Na2SO4
  3. customAfter removal of solvents the residue
  4. customwas purified by chromatography on silica gel (ethyl acetate/n-heptane 1:5)
  5. customto yield 3.12 g (28%)

Sources & evidence

ORD record
ord-1f1e5fa246a5440a9083e1152278fdbf
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

Loading…