Acetic Acid → HCID 549741, compound

HRID 1076794Notes

Reaction equation

HRID 1076794 reaction equation
Br[CH:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]([C:10](=[O:14])[CH:11]=[CH:12][CH3:13])=[C:3]1[CH3:15].C(O)(=[O:18])C>O>[CH3:15][C:3]1[C:2](=[O:18])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]=1[C:10](=[O:14])[CH:11]=[CH:12][CH3:13]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 54412118HCID 54412118, compound

Product 1

HCID 549741HCID 549741, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

125 g of crude 3-bromo-2,6,6-trimethyl-1-(but-2-enoyl)-cyclohex-1-ene [prepared under letter a] were added dropwise to a mixture of 100 g (1 Mole) CrO3, 100 ml acetic acid and 100 ml of water, kept at 20°-25°. After addition of the reactants the reaction mixture was heated under stirring at 40° for 30 min., and finally diluted with 1 l of water. After neutralization of the reactin mixture by means of a 10 % aqueous solution of NaOH, the obtained mixture was submitted to a steam distillation. 3 l of the thus obtained distillate were then extracted with ether (3 × 500 ml), the organic layer was washed with water, dryed over Na2SO4 and finally concentrated under reduced pressure. There were thus obtained 68.2 g (73 %) of a semi-cristalline product, b.p. 71°-116°/o.01 Torr, which was finally cristallized in hexane to afford 51.3 g (55 %) of pure 2,6,6-trimethyl-1-(but-2-enoyl)-cyclohex-1-en-3-one, m.p. 68°-69°.

Workup

  1. customkept at 20°-25°
  2. additionAfter addition of the reactants the reaction mixture
  3. temperaturewas heated
  4. distillationAfter neutralization of the reactin mixture by means of a 10 % aqueous solution of NaOH, the obtained mixture was submitted to a steam distillation
  5. extraction3 l of the thus obtained distillate were then extracted with ether (3 × 500 ml)
  6. washthe organic layer was washed with water
  7. concentrationfinally concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d278737f14e442e82a2c2c05c1a40c2
Source dataset
uspto-grants-1976_05
Patent number
US03957877

Reaction notes

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