1-Butanol → HCID 544772, compound

HRID 1461203Notes

Reaction equation

HRID 1461203 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>CCOCC>[CH2:1]([O:5][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][Br:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 1049PyridineHCID 898486-Bromohexanoyl chloride

Product 1

HCID 544772HCID 544772, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cooled, stirred solution of 39 g (0.52 mol) of butanol and 42 g (0.52 mol) of pyridine in 550 mL of ether was added dropwise 100 g (0.47 mol) of 6-bromohexanoylchloride. The reaction mixture was stirred for 1 hour and then filtered. The filtrate was washed with water, 5% NaHCO3, and again with water. The organic layer was dried (MgSO4), the solvent was removed by rotary evaporation, and the residue was distilled at reduced pressure, bp 120°-125° C. (0.1 mm). A colorless oil was obtained, mass 111 g (94%).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water, 5% NaHCO3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent was removed by rotary evaporation
  5. distillationthe residue was distilled at reduced pressure, bp 120°-125° C. (0.1 mm)
  6. customA colorless oil was obtained

Sources & evidence

ORD record
ord-a6c144d468d7484a9f8d8d1b9ef8bcc0
Source dataset
uspto-grants-1991_12
Patent number
US05075043

Reaction notes

Loading…