Dimethylformamide → 1-(Chloromethyl)-3-(2-propen-1-yloxy)benzene

HRID 2395002Notes

Reaction equation

HRID 2395002 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8]O)[CH:2]=[CH2:3].S(Cl)([Cl:15])=O.CN(C=O)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][Cl:15])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 28065595{3-[(Prop-2-en-1-yl)oxy]phenyl}methanol

Product 1

HCID 141693671-(Chloromethyl)-3-(2-propen-1-yloxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-allyloxybenzyl alcohol (7.2 g) in dichloromethane (100 ml) at 0° C. was added thionyl chloride (4.8 ml) in dichloromethane dropwise and a drop of DMF and the mixture stirred at ambient temperature for 1.5 hours, and poured into cold sodium bicarbonate solution. The organic layer was washed with sodium bicarbonate (2×100 ml), dried (magnesium sulphate), filtered and evaporated to give 3-allyloxybenzyl chloride (8.3 g).

Workup

  1. washThe organic layer was washed with sodium bicarbonate (2×100 ml)
  2. dry with materialdried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a86e45a81d2f4662bf6e602be507eaed
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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