Ammonium Acetate → HCID 20193837, compound

HRID 2118477Notes

Reaction equation

HRID 2118477 reaction equation
C[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12]([CH3:14])=O.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[NH2:21][CH:12]([CH3:14])/[CH:11]=[CH:10]/[C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][C:7]=1[CH3:2]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 638014I2-IononeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 20193837HCID 20193837, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of β-ionone (10.0 g., 52 mmol), ammonium acetate (40.0 g., 520 mmol) and sodium cyanoborohydride (3.27 g., 52 mmol) in methanol (150 ml) is stirred at room temperature for 3 days. The mixture is then made acidic to a pH less than 2 with concentrated hydrochloric acid, and most of the solvent is evaporated under vacuum. Water (150 ml) is added and the solution is washed with two 50 ml portions of ether. The aqueous solution is then made basic to pH greater than 10 with solid sodium hydroxide. The mixture is extracted with two 50 ml portions of ether, and the combined extracts washed with saturated sodium chloride solution, dried over magnesium sulfate, and the solvent is evaporated to yield a colorless oil (2.3 g.). The product is isolated by HPLC on a bonded C18 reverse phase column using methanol as the eluent to yield approximately 1 g. of a colorless oil.

Workup

  1. custommade acidic to a pH less than 2 with concentrated hydrochloric acid, and most of the solvent is evaporated under vacuum
  2. additionWater (150 ml) is added
  3. washthe solution is washed with two 50 ml portions of ether
  4. extractionThe mixture is extracted with two 50 ml portions of ether
  5. washthe combined extracts washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent is evaporated
  8. customto yield a colorless oil (2.3 g.)
  9. customThe product is isolated by HPLC on
  10. customto yield approximately 1 g

Sources & evidence

ORD record
ord-ea3563efe92d43a59200e8beb973feb5
Source dataset
uspto-grants-1987_07
Patent number
US04678675

Reaction notes

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