1-Butanol → HCID 66739524, compound

HRID 1640348Notes

Reaction equation

HRID 1640348 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.C(O)CCC>O.C1(C)C=CC=CC=1>[C:3]([OH:5])(=[O:4])[CH2:2][CH2:6][CH3:7].[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 145742L-Proline

Product 1

HCID 66739524HCID 66739524, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

34.5 g of proline was suspended in a solution of 35 g of concentrated sulfuric acid, 40 mL water, 120 mL of butanol, and 200 mL of toluene in a 500 mL round bottom flask equipped with a condenser and a Dean-Stark apparatus. The resulting solution was heated at reflux temperature until no more water could be distilled. The resulting solution was then cooled to room temperature, washed with saturated aqueous sodium bicarbonate to neutralize acidic impurities, washed with saturated Brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the resulting liquid distilled to provide proline butanoate as a colorless liquid.

Workup

  1. customequipped with a condenser
  2. temperatureThe resulting solution was heated
  3. distillationcould be distilled
  4. washwashed with saturated aqueous sodium bicarbonate
  5. washwashed with saturated Brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. distillationthe resulting liquid distilled

Sources & evidence

ORD record
ord-ba0360d2d4e84a63811f357553128e2f
Source dataset
uspto-grants-2012_02
Patent number
US08114440B2

Reaction notes

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