Triethylamine → Methyl 4-(chloromethyl)cinnamate

HRID 618763Notes

Reaction equation

HRID 618763 reaction equation
O[CH2:2][C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.CS([Cl:26])(=O)=O>C(Cl)Cl>[Cl:26][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54313853Methyl 4-(hydroxymethyl)cinnamate

Product 1

HCID 53426371Methyl 4-(chloromethyl)cinnamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 4-(hydroxymethyl)cinnamate (4.1 g), triethylamine (3.1 ml) and methylene chloride (50 ml) was added dropwise under ice cooling methanesulfonyl chloride (1.7 ml), and the mixture was stirred at room temperature for 1.5 hours. Evaporation of the reaction solution gave a residue, which was then chromatographed on silica gel column (eluent: methylene chloride) to give methyl 4-(chloromethyl)cinnamate (2.57 g).

Workup

  1. additionwas added dropwise under ice
  2. customEvaporation of the reaction solution
  3. customgave a residue, which
  4. customwas then chromatographed on silica gel column (eluent: methylene chloride)

Sources & evidence

ORD record
ord-f3a3de5552354205a5016cd709b7de46
Source dataset
uspto-grants-1999_09
Patent number
US05955505

Reaction notes

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