Sulfuric Acid → HCID 53760255, compound

HRID 328662Notes

Reaction equation

HRID 328662 reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:10][C:11](=[O:23])[CH:12]=[C:13]([CH2:21][CH3:22])[CH:14]([CH3:20])[CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:7][CH2:8][CH3:9]>C(O)=O>[CH2:6]([O:10][C:11]([CH:12]1[C:17]([CH3:19])([CH3:18])[CH2:16][CH2:15][C:14]([CH3:20])=[C:13]1[CH2:21][CH3:22])=[O:23])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 54574149HCID 54574149, compound

Product 1

HCID 53760255HCID 53760255, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 81 ml of concentrated formic acid and 9 ml of concentrated sulphuric acid is cooled to 5°-10° C and there are cautiously added at this temperature 10 g (39.7 mmol) of 3-ethyl-4,7-dimethyl-2,6-octadienoic acid n-butyl ester. The mixture is left to come to room temperature and then stirred at room temperature for ca 1 hour. The mixture is then poured on to ice and extracted three times with hexane. The combined hexane solutions are washed once with water, twice with sodium bicarbonate solution and three times with water, dried over sodium sulphate and concentrated. The crude product (9.1 g) is fractionally distilled. There are obtained 6.9 g (69%) of pure 2-ethyl-3,6,6-trimethyl-2-cyclohexene-1-carboxylic acid n-butyl ester of boiling point 75°-74° C/0.03 mm Hg; nD 20 = 1.4663. The ester has a powerful balsamic and spicy odor with a slight buttery undertone.

Workup

  1. temperatureis cooled to 5°-10° C
  2. waitThe mixture is left
  3. customto come to room temperature
  4. additionThe mixture is then poured on to ice
  5. extractionextracted three times with hexane
  6. washThe combined hexane solutions are washed once with water, twice with sodium bicarbonate solution and three times with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. distillationThe crude product (9.1 g) is fractionally distilled

Sources & evidence

ORD record
ord-0b6006f312384e8485fa4ccbf1e5c402
Source dataset
uspto-grants-1977_04
Patent number
US04018718

Reaction notes

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