Hydrochloric Acid → Propionic Acid

HRID 616973Notes

Reaction equation

HRID 616973 reaction equation
[OH:1][C:2]1([NH:5][C:6]2([OH:9])[CH2:8][CH2:7]2)[CH2:4][CH2:3]1.[ClH:10].[Cl-].[OH:12]C1([NH2+]C2(O)CC2)CC1>>[Cl-:10].[OH:1][C:2]1([NH3+:5])[CH2:4][CH2:3]1.[C:6]([OH:9])(=[O:12])[CH2:8][CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20367051HCID 20367051, compoundHCID 20367053HCID 20367053, compound

Product 2

HCID 1032Propionic AcidHCID 70620051HCID 70620051, compound

Procedure

To bis(1-hydroxycyclopropyl)-amine (50 mg) [W. J. M. van Tilborg, Thesis, Amsterdam 1971] in D2O is added a small excess of conc. HCl. The NMR-spectrum shows a singlet for bis(1-hydroxycyclopropyl)-ammonium chloride (δD 2O = 1.25 (s, 4H)). The sample is heated at 80° for 4 hr yielding 1-hydroxycyclopropylammonium chloride (δD 2O = 1.17 (s, 4H)) and propionic acid. (The decomposition is much faster at higher HCl concentrations). Evaporation gives, as an oil, 1-hydroxycyclopropylammonium chloride.

Workup

  1. temperatureThe sample is heated at 80° for 4 hr

Sources & evidence

ORD record
ord-637ea178c7b3462eaae95879cfde85ac
Source dataset
uspto-grants-1978_02
Patent number
US04076840

Reaction notes

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