Hydrochloric Acid → HCID 21249534, compound

HRID 1531597Notes

Reaction equation

HRID 1531597 reaction equation
[O:1]=[C:2]1[CH:16](C(OCC)=O)[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1.C(O)C.Cl.C(OCC)C>O>[C:2]1(=[O:1])[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 131722423HCID 131722423, compound

Product 1

HCID 21249534HCID 21249534, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude ethyl 15-oxocyclopentadeca-3E,11E-dienecarboxylate (prepared as described above) was treated with ethanol (10 ml) and 3N aqueous hydrochloric acid (20 ml) and heated to reflux for 20 hours. The solution was cooled and diethyl ether and water were added. The layers were separated and the organic fraction was dried with magnesium sulfate, filtered and evaporated to provide a brown oil which was purified by column chromatography (10% diethyl ether/hexane) to afford cyclopentadeca-4E,12E-dien-1-one (0.50 g, 17% yield from diethyl hexadeca-4E,12E-diene-1,16-dioate). C15H24O (220.36 g/mole). 1HNMR (500 MHz, CDCl3): 1.15 (m, 4H), 1.34 (m, 4H). 1.97 (m, 4H), 2.24 (m, 4H), 2.45 (m, 4H), 5.30 (m, 2H), 5.39 (m, 2H) ppm. 13CNMR (125 MHz, CDCl3): 26.7, 27.4, 28.4, 31.2, 42.8, 129.2, 131.3, 210.4 ppm. IR (νmax(cm−1)): 2990, 2950, 2910, 2850, 1720, 1440, 1400, 1360, 1080, 980, 720. MS (m/z): 220(M+), 177, 163, 149, 135, 121, 109, 95, 81, 67, 55, 41.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. temperatureThe solution was cooled
  4. customThe layers were separated
  5. dry with materialthe organic fraction was dried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto provide a brown oil which
  9. customwas purified by column chromatography (10% diethyl ether/hexane)

Sources & evidence

ORD record
ord-76405a4f8d2d4df7af2ad00c47499039
Source dataset
uspto-grants-2001_03
Patent number
US06200254B1

Reaction notes

Loading…