Diethyl Ether → 2-(7-Hydroxyheptyl)cyclopent-2-en-1-one

HRID 442441

Reaction equation

HRID 442441 reaction equation
O1CCCCC1O[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15].O1CCN(C2CCCC=2)CC1.[C:27]1(=[O:32])[CH2:31][CH2:30][CH2:29][CH2:28]1.C(OCC)C>C1C=CC=CC=1>[OH:32][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:8][CH2:9][C:10]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8452CyclopentanoneHCID 702941-MorpholinocyclopenteneHCID 1821847-(Oxan-2-yloxy)heptanal

Product 1

HCID 205354882-(7-Hydroxyheptyl)cyclopent-2-en-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(2-tetrahydropyranyloxy)heptanal (22 g.) and 1-morpholinocyclopentene, i.e. the morpholine enamine of cyclopentanone, (21.4 g.) in benzene (25 ml.) was heated under reflux for 12 hours under nitrogen, and the water liberated was continuously removed with a Dean and Stark head. Benzene (10 ml.) and then, dropwise, 18% hydrochloric acid (28 ml.) were added and the mixture was stirred for 2 hours. The organic layer was separated and evaporated. Concentrated hydrochloric acid (72 ml.) was added to the residue. The mixture was heated at 100° C. for 1 hour, and then the solution was concentrated to give an oil. Diethyl ether was added, and the ether solution was washed with aqueous sodium bicarbonate and then water, and dried over sodium sulphate. The solvent was evaporated and the residue was distilled under reduced pressure to give 2-(7-hydroxyheptyl)cyclopent-2-enone (11.7 g.), b.p. 125°- 170° C./0.15 mm.Hg, nD25 = 1.490, Λmax 228mμ (ethanol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours under nitrogen
  3. customthe water liberated was continuously removed with a Dean and Stark head
  4. additionBenzene (10 ml.) and then, dropwise, 18% hydrochloric acid (28 ml.) were added
  5. customThe organic layer was separated
  6. customevaporated
  7. additionConcentrated hydrochloric acid (72 ml.) was added to the residue
  8. concentrationthe solution was concentrated
  9. customto give an oil
  10. washthe ether solution was washed with aqueous sodium bicarbonate
  11. dry with materialwater, and dried over sodium sulphate
  12. customThe solvent was evaporated
  13. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-39f1c1dd391b430e92cc7f3d18731b51
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Linked notes

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