Isopropanol → (-) Ammonium(4S)-p-menth-1-ene-7-sulfonate

HRID 364857

Reaction equation

HRID 364857 reaction equation
C(O)(C)C.[CH3:5][C:6]1([CH3:14])[CH:12]2[CH2:13][CH:7]1[CH2:8][CH2:9][C:10]2=[CH2:11].[S:15](=[O:18])([OH:17])[O-:16].[NH4+:19]>O>[C:10]1([CH2:11][S:15]([O-:18])(=[O:17])=[O:16])[CH2:12][CH2:13][C@H:7]([CH:6]([CH3:14])[CH3:5])[CH2:8][CH:9]=1.[NH4+:19]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14896Beta-PineneHCID 10441651Ammonium Bisulfite

Product 1

HCID 86740958(-) Ammonium(4S)-p-menth-1-ene-7-sulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1 liter flask equipped with magnetic stirrer were placed 450 ml isopropanol, 240 ml water and 54.4 grams (0.4 mole) β-pinene. Ammonium bisulfite, 105 grams (45%) was then added thereto. The mixture was stirred at 40°-45° C. for 22 hours. Thereafter, the solution was evaporated to dryness. Residue was extracted with methanol. The methanolic solution was filtered, and the resultant filtrate evaporated to dryness. Obtained were 84 grams product (85.8% purity; 77% yield).

Workup

  1. customInto a 1 liter flask equipped with magnetic stirrer
  2. customThereafter, the solution was evaporated to dryness
  3. extractionResidue was extracted with methanol
  4. filtrationThe methanolic solution was filtered
  5. customthe resultant filtrate evaporated to dryness
  6. customObtained

Sources & evidence

ORD record
ord-67e9e610eb794563b4d1adf68a722109
Source dataset
uspto-grants-1986_08
Patent number
US04606851

Linked notes

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