Acetic Acid → HCID 21453522, compound

HRID 436248Notes

Reaction equation

HRID 436248 reaction equation
[CH3:1][C@@:2]12[CH2:11][CH2:10][CH2:9][C@H:8]([CH3:12])[C:7]1=[CH:6][C:5](=[O:13])[CH2:4][CH2:3]2.CC([O-])(C)C.[K+].C(O)(=O)C.C([O-])(O)=O.[Na+]>C(O)(C)(C)C>[CH3:1][C:2]12[CH2:11][CH2:10][CH2:9][C:8]([CH3:12])=[C:7]1[CH2:6][C:5](=[O:13])[CH2:4][CH2:3]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 6428338HCID 6428338, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21453522HCID 21453522, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 2.0 g (11.5 mM) of trans-6,10-dimethyl-bicyclo[4.4.0]dec-1-en-3-one and 12.0 g (ca. 110 mM) of potassium ter-butylate in 75 ml of ter-butanol, has been stirred during 2 hr at room temperature under an inert atmosphere of nitrogen. 400 ml of a 10% aqueous solution of acetic acid were then added thereto and the thus obtained mixture rapidly neutralized with a saturated aqueous solution of NaHCO3. By extraction with ether followed by washing, drying, evaporation and purification by column chromatography on silicagel (elution with CH2Cl2), there were obtained 1.80 g (90% yield) of the desired product. IR (neat) : 1710, 1600 cm-1NMR (CCl4) : 1.20 (3H,s); 1.58 (3H, large s); 2.27 (2H,t,J=5 cps); 3.10 (2H,m) δ ppm MS : M+ = 178 (57); m/e = 163 (100), 123 (45), 93 (42).

Workup

  1. extractionBy extraction with ether
  2. washby washing
  3. customdrying
  4. customevaporation and purification by column chromatography
  5. washon silicagel (elution with CH2Cl2)

Sources & evidence

ORD record
ord-18ac633e53074bfa8269b451aea65918
Source dataset
uspto-grants-1977_02
Patent number
US04008184

Reaction notes

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