Pyridine → ZR 2646

HRID 328152Notes

Reaction equation

HRID 328152 reaction equation
N1C=CC=CC=1.[C:7](Cl)(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].Cl.N1C=CC=CC=1.[CH2:21]([O:23][C:24]([C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][CH:32]([OH:35])[CH2:33][CH3:34])=[CH:28][CH:27]=1)=[O:25])[CH3:22]>>[C:7]([O:35][CH:32]([CH2:33][CH3:34])[CH2:31][O:30][C:29]1[CH:36]=[CH:37][C:26]([C:24]([O:23][CH2:21][CH3:22])=[O:25])=[CH:27][CH:28]=1)(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 4

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 10176127Pyridinium chlorideHCID 21444117Ethyl 4-(2-hydroxybutoxy)benzoate

Product 1

HCID 162792ZR 2646Yield 89%

Procedure

In pyridine (10ml) 1.2 g (5 mmol) of 1-(p-ethoxycarbonyl-phenoxy)-butan- 2-ol was dissolved and to this solution was gradually added 0.6 g (5 mmol) of pivaloyl chloride cooling in an ice bath. The mixture was stirred at room temperature for 3 hours after the addition was completed. During the course of the reaction pyridine hydrochloride precipitated. The reaction mixture was then poured in ice water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated to afford 1.6g of 1-(p-ethoxycarbonyl-phenoxy)-butan-2-ol pivalate (compound No. 1) in a yield of 89% as a light yellow viscous oily substance.

Workup

  1. additionafter the addition
  2. customprecipitated
  3. additionThe reaction mixture was then poured in ice water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0f22a9d3d5004617b51f20e6cd35464c
Source dataset
uspto-grants-1977_04
Patent number
US04016186

Reaction notes

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