Sulfuric Acid → HCID 20322317, compound

HRID 372894Notes

Reaction equation

HRID 372894 reaction equation
[N+](=[CH:3][C:4]([CH:6]([CH2:18][CH2:19][CH2:20][CH:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])=[N-].S(=O)(=O)(O)[OH:32]>O1CCOCC1.O>[C:4]([CH:6]([CH2:18][CH2:19][CH2:20][CH:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:5])[CH2:3][OH:32]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 54204114HCID 54204114, compound

Product 1

HCID 20322317HCID 20322317, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A clear, yellow solution of ethyl 8-diazoacetyl-12-acetoxyheptadecanoate (8.4 g., 0.02 mole) in dioxane (50 ml.) is vigorously stirred at 20° and treated with 2N sulfuric acid (30 ml.) added dropwise over 5 minutes. The resulting turbid solution is warmed to and maintained at 65° for 30 minutes. The reaction solution is cooled to 20°, diluted with water to a total volume of one liter and extracted with ether (5 × 200 ml.). The organic extract is washed with water (2 × 200 ml.), 5% aqueous sodium bicarbonate (200 ml.), water (200 ml.), and saturated brine (2 × 200 ml.), dried over sodium sulfate and filtered. Evaporation (in vacuo at 40°-65°) of the filtrate gives the title compound as a deep yellow oil (7.9 g., 96%), pmr (CDCl3) δ 0.86 (3H,t), 1.28 (27H,e), 2.0 (3H,s), 2.25 (3H,t), 3.36 (H,b), 4.10 (2H,q), 4.21 (2H,s) and 4.84 (H,b).

Workup

  1. additionadded dropwise over 5 minutes
  2. temperatureThe resulting turbid solution is warmed to and
  3. temperaturemaintained at 65° for 30 minutes
  4. temperatureThe reaction solution is cooled to 20°
  5. extractionextracted with ether (5 × 200 ml.)
  6. extractionThe organic extract
  7. washis washed with water (2 × 200 ml.), 5% aqueous sodium bicarbonate (200 ml.), water (200 ml.), and saturated brine (2 × 200 ml.)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customEvaporation (in vacuo at 40°-65°) of the filtrate

Sources & evidence

ORD record
ord-0ec4b3ac373341f48155d2f8b77b6269
Source dataset
uspto-grants-1978_05
Patent number
US04092356

Reaction notes

Loading…