Pyridine → 2-Oxopropyl decanoate

HRID 464145

Reaction equation

HRID 464145 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:13][CH2:14][C:15](=[O:17])[CH3:16].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]([O:13][CH2:14][C:15](=[O:17])[CH3:16])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8299HydroxyacetoneHCID 66982Decanoyl chloride

Product 1

HCID 137501072-Oxopropyl decanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Monohydroxyacetone was distilled prior to use. Chloroform was distilled from phosphorus pentoxide prior to use. Decanoyl chloride (65 cm3, 0.3146 mole) was added dropwise to stirred solution of monohydroxyacetone (21.8 cm3, 0.3146 mole) and anydrous pyridine (25.4 cm3, 0.3146 mole) in anhydrous chloroform (500 cm3). During the addition the solution was maintained in an ice bath. The mixture was then stirred at room temperature overnight. The solution was washed with water (4×200 cm3) and saturated sodium chloride solution (200 cm3). The organic phase was dried over sodium sulphate and evaporated in vacuo. The resulting oil was distilled to yield 1-decanoyloxypropan-2-one as a mobile liquid, bp 154°-60° (1 mm) (52.4 g, 0.230 mole, 73%),ir (neat) 2860, 1700, 1400, 1340, 1150, 1110 and 1050 cm-1 ; pmr (CDCI3) δ 4.6 (s, 2 H), 2.4 (t, 2 H), 2.1 (s, 3 H), 1.8-1.0 (bm, 14 H) and 0.9 (t, 3 H) ppm.

Workup

  1. distillationMonohydroxyacetone was distilled
  2. distillationChloroform was distilled from phosphorus pentoxide
  3. additionDuring the addition the solution
  4. temperaturewas maintained in an ice bath
  5. washThe solution was washed with water (4×200 cm3) and saturated sodium chloride solution (200 cm3)
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customevaporated in vacuo
  8. distillationThe resulting oil was distilled

Sources & evidence

ORD record
ord-a722bc3546264bc29eb96482df1c35fb
Source dataset
uspto-grants-1985_10
Patent number
US04546197

Linked notes

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