Ethanol → HCID 54011146, compound

HRID 373478Notes

Reaction equation

HRID 373478 reaction equation
C[C:2]1[C:6]([CH3:8])([CH3:7])[CH:5]([CH2:9][C:10]([OH:12])=[O:11])[CH2:4][CH:3]=1.[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1.[CH2:24](O)C>CCCCCCC>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][CH:5]1[CH2:4][C:3]([CH3:24])=[CH:2][C:6]1([CH3:7])[CH3:8])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 117235(2,2,3-Trimethylcyclopent-3-en-1-yl)acetic acid

Product 1

HCID 54011146HCID 54011146, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
71 °C

Procedure

A solution containing a mixture (99 g) of γ-campholenic acid (56%) and α-campholenic acid (43%), p-toluenesulfonic acid (2 g), ethanol (750 ml) and heptane (750 ml) was kept at reflux (71° C.) for 16 hours, while the condensate was perculated through a layer of molecular sieves (3 Å) (100 g). The solvent was then removed, the residue taken up in CH2Cl2 (1 liter) and the solution extracted with ice cold 5% aqueous sodium hydroxide (1 liter) and water (2×500 ml). Concentration of the dried CH2Cl2 solution gave a crude oil (115 g), which was distilled through a 9" glass packed column to give 95 g of a colorless liquid; bp 73°-75° C. @ 1.5 mm Hg; analysis: (CW 20M fused silica column, 120°-190° C.; 5° C./min.) 60% ethyl γ-campholenate and 40% ethyl α-campholenate; odor: fruity, berry; flavor: sweet, fruity, berry.

Workup

  1. customThe solvent was then removed
  2. extractionthe solution extracted with ice cold 5% aqueous sodium hydroxide (1 liter) and water (2×500 ml)
  3. customConcentration of the dried CH2Cl2 solution gave a crude oil (115 g), which
  4. distillationwas distilled through a 9" glass

Sources & evidence

ORD record
ord-aa938e6ff2dc4c98b1d552ed406e609d
Source dataset
uspto-grants-1992_11
Patent number
US05164364

Reaction notes

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