Pyridine → 1-Hexanol, 6-chloro-, 1-acetate

HRID 1981560Notes

Reaction equation

HRID 1981560 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=CC=1>C(OCC)C>[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 748286-Chloro-1-hexanol

Product 1

HCID 1702851-Hexanol, 6-chloro-, 1-acetateYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 100 ml of 6-chloro-1-hexanol, 85 ml of acetic anhydride and 67 ml of pyridine in 300 ml of dry ethyl ether was stirred at room temperature for 1 h. The reaction mixture was washed 3 times with 100 ml of water and twice with 100 ml of saturated brine, dried over Na2SO4, filtered and evaporated. Distillation afforded 133 g of 6-chlorohexanol acetate (99%), b.p. 132° C. (10 mm).

Workup

  1. washThe reaction mixture was washed 3 times with 100 ml of water
  2. dry with materialtwice with 100 ml of saturated brine, dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. distillationDistillation

Sources & evidence

ORD record
ord-b8cbff4fc81f4631942b9af56554153e
Source dataset
uspto-grants-1986_06
Patent number
US04593029

Reaction notes

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