Hydrochloric Acid → 5-Hydroxy-4-propylfuran-2(5H)-one

HRID 1021011Notes

Reaction equation

HRID 1021011 reaction equation
N1CCOCC1.[C:7]([OH:11])(=[O:10])[CH:8]=O.[CH3:12][CH2:13][CH2:14][CH2:15][CH:16]=[O:17].Cl>CCCCCCC>[OH:17][CH:16]1[O:11][C:7](=[O:10])[CH:8]=[C:15]1[CH2:14][CH2:13][CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 760Glyoxylic AcidHCID 8063PentanalHCID 8083Morpholine

Product 1

HCID 128648005-Hydroxy-4-propylfuran-2(5H)-one

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

Heptane (394 mL) and morpholine (127.5 mL) are introduced in a reactor while stirring. The mixture is cooled to 0° C. and glyoxylic acid (195 g, 150 mL, 50 wt % in water) is added. The mixture is heated to 20° C. during 1 hour and then n-valeraldehyde (148.8 mL) is added. The reaction mixture is heated at 45° C. during 20 hours. After cooling down to 20° C., a 37% aqueous solution of hydrochloric acid (196.9 mL) is slowly added to the mixture, which is then stirred during 2 hours.

Workup

  1. temperatureThe mixture is heated to 20° C. during 1 hour
  2. temperatureThe reaction mixture is heated at 45° C. during 20 hours
  3. temperatureAfter cooling down to 20° C.
  4. stirringis then stirred during 2 hours

Sources & evidence

ORD record
ord-42843905deed4945b53a704bb3882efc
Source dataset
uspto-grants-2014_05
Patent number
US08716520B2

Reaction notes

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