Triethylamine → 2-Propenoic acid, 3-hydroxypropyl ester

HRID 1672105Notes

Reaction equation

HRID 1672105 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[C:13](Cl)(=[O:16])[CH:14]=[CH2:15]>C1COCC1>[C:13]([O:4][CH2:3][CH2:2][CH2:1][OH:5])(=[O:16])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104421,3-PropanediolHCID 13140Acryloyl chloride

Product 1

HCID 331012-Propenoic acid, 3-hydroxypropyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3-Propanediol (by Tokyo Kasei) and triethylamine were dissolved in THF, and in an ice-water bath, acryloyl chloride was added thereto. After the reaction, the reaction liquid was washed with aqueous saturated sodium hydrogencarbonate solution added thereto, and then the organic layer was washed with 1 N hydrochloric acid and saturated saline water. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The crude product was purified through silica gel column chromatography to obtain 32 g of 3-hydroxypropyl acrylate (yield: 50%).

Workup

  1. customAfter the reaction
  2. customthe reaction liquid
  3. washwas washed with aqueous saturated sodium hydrogencarbonate solution
  4. additionadded
  5. washthe organic layer was washed with 1 N hydrochloric acid and saturated saline water
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. customthe solvent was evaporated away
  8. customThe crude product was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-80aef05fcda446929cd1322625e1c604
Source dataset
uspto-grants-2011_08
Patent number
US07998542B2

Reaction notes

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