Ethanol → HCID 21727313, compound

HRID 399711Notes

Reaction equation

HRID 399711 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[O:10][CH2:11][C:12]([OH:14])=[O:13])=[N+:2]=[N-:3].S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[CH2:20]([O:13][C:12](=[O:14])[CH2:11][O:10][C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:4]1[N:1]=[N+:2]=[N-:3])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 15617698HCID 15617698, compound

Product 1

HCID 21727313HCID 21727313, compoundYield 68%

Procedure

A solution of trans-2-(2'-azidocyclohexyloxy)-acetic acid (11.16 g, 56 mmoles) and concentrated sulphuric acid (0.8 ml) in anhydrous ethanol (30 ml) was heated for 3 hours at reflux temperature, then the mixture was poured into ice water (150 ml) and extracted with n-hexane (4×60 ml). The combined hexane phases were dried over MgSO4, filtered and the solvent was evaporated. The crude product was distilled in vacuo (boiling point: 129° C./0.67 mbar), yielding 8.6 g (68%) of the title compound in the form of a yellow oil.

Workup

  1. temperatureat reflux temperature
  2. extractionextracted with n-hexane (4×60 ml)
  3. dry with materialThe combined hexane phases were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. distillationThe crude product was distilled in vacuo (boiling point: 129° C./0.67 mbar)

Sources & evidence

ORD record
ord-e1461c6004904dd797a914baed2cc3b5
Source dataset
uspto-grants-1998_10
Patent number
US05824652

Reaction notes

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