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

HRID 426779

Reaction equation

HRID 426779 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 (21.4 g), i.e. the morpholine enamine of cyclopentanone, 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) and butanol (300 ml) were 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 228 mμ (ethanol).

Workup

  1. temperatureunder reflux for 12 hours under nitrogen
  2. customthe water liberated was continuously removed with a Dean and Stark head
  3. additionBenzene (10 ml) and then, dropwise, 18% hydrochloric acid (28 ml) were added
  4. customThe organic layer was separated
  5. customevaporated
  6. additionConcentrated hydrochloric acid (72 ml) and butanol (300 ml) were added to the residue
  7. concentrationthe solution was concentrated
  8. customto give an oil
  9. washthe ether solution was washed with aqueous sodium bicarbonate
  10. dry with materialwater, and dried over sodium sulphate
  11. customThe solvent was evaporated
  12. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-9e4474fc85314902978f35ec2cf72e32
Source dataset
uspto-grants-1979_10
Patent number
US04171375

Linked notes

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