Acetic Acid → HCID 131722423, compound

HRID 1531596Notes

Reaction equation

HRID 1531596 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:28][CH2:29][CH3:30])(=[O:27])[CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]/[CH2:20][CH2:21][C:22]([O:24]CC)=O.C(O)(=O)C.O>C1(C)C=CC=CC=1>[O:24]=[C:22]1[CH:8]([C:7]([O:28][CH2:29][CH3:30])=[O:27])[CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 131722422HCID 131722422, compound

Product 1

HCID 131722423HCID 131722423, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a flask containing a solution of potassium t-butoxide (6.30 g, 61.1 mmole) in toluene (80 ml), heated to reflux, was added slowly (via syringe pump over 15 hours) a solution of diethyl hexadeca-4E,12E-diene-1,16-dioate (4.32 g, 12.8 mmole) in toluene (10 ml). After the addition was complete the mixture was maintained at reflux for an additional 5 hours. The reaction mixture was cooled to room temperature and to the mixture was added acetic acid and then water. To the mixture was then added diethyl ether, the layers separated and the organic layer was dried with sodium sulfate and evaporated to provide the crude ethyl 15-oxocyclopentadeca-3E,11E-dienecarboxylate which was used directly in the next step. C18H28O3 (292.42 g/mole). 1HNNR (500 MHz, CDCl3): 1.16 (m, 4H), 1.23 (t, 3H), 1.34 (m, 4H), 1.99 (m, 4h), 2.13 (m, 1H), 2.40 (m, 2H), 2.55 (m, 1H), 2.70 (m, 2H), 3.50 (dd, 1H), 4.13 (q, 2H), 5.40 (m, 4H) ppm. 13CNMR (125 MHz, CDCl3): 14.1, 26.2, 27.0, 27.4, 27.7, 28.6, 31.0, 31.1, 31.2, 43.6, 58.4, 61.3, 126.3, 129.1, 131.6, 133.6, 169.5, 204.6 ppm. IR (νmax(cm−1)): 2990, 2940, 2910, 2850, 1745, 1720, 1640, 1440, 1370, 1260, 1040, 970, 860. MS (m/z): 292(M+), 247, 163, 149, 135, 121, 107, 95, 81, 67, 55, 41.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. additionAfter the addition
  4. temperaturewas maintained
  5. temperatureat reflux for an additional 5 hours
  6. customadded diethyl ether, the layers separated
  7. dry with materialthe organic layer was dried with sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-d2a386248c9444f9bba3c68a3da924d6
Source dataset
uspto-grants-2001_03
Patent number
US06200254B1

Reaction notes

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