Triethylamine → HCID 13668181, compound

HRID 382225Notes

Reaction equation

HRID 382225 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].C(N(CC)CC)C.[C:14](Cl)(=[O:17])[CH:15]=[CH2:16]>ClCCl>[C:14]([O:5][CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])(=[O:17])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111733-Methyl-2-buten-1-OLHCID 13140Acryloyl chloride

Product 1

HCID 13668181HCID 13668181, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1-liter flask was charged with 43.9 g (0.51 mol) of 3-methyl-2-buten-1-ol, 51.6 g (0.51 mol) of triethylamine and 300 ml of dichloromethane, and the mixture was cooled down to 0° C. While stirring the mixture at 0° C., 45.3 g (0.50 mol) of acryloyl chloride were added dropwise over 1 hour, and the mixture was stirred additionally for 5 hours at room temperature. Solids were separated by filtration from the resultant reaction mixture, and the filtrate was washed 3 times with water and then distilled in the presence of 5 g of p-methoxyphenol to obtain 50.5 g of 3-methyl-2-butenyl acrylate.

Workup

  1. stirringthe mixture was stirred additionally for 5 hours at room temperature
  2. customSolids were separated by filtration from the resultant
  3. customreaction mixture
  4. washthe filtrate was washed 3 times with water
  5. distillationdistilled in the presence of 5 g of p-methoxyphenol

Sources & evidence

ORD record
ord-9760a01837cc4b40a24c5b3f7eadb692
Source dataset
uspto-grants-2001_10
Patent number
US06309795B1

Reaction notes

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