Benzene → 2-(6-Hydroxyhexyl)-2-cyclopenten-1-one

HRID 1581100Notes

Reaction equation

HRID 1581100 reaction equation
O1CCCCC1O[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14].C([O:17][CH2:18][CH3:19])C.[CH:20]1[CH:25]=CC=C[CH:21]=1>>[OH:17][CH2:18][CH2:19][CH2:21][CH2:20][CH2:25][CH2:8][C:9]1[C:13](=[O:14])[CH2:12][CH2:11][CH:10]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 3283Diethyl EtherHCID 108673416-(2-Tetrahydropyranyloxy)hexanal

Product 1

HCID 215614872-(6-Hydroxyhexyl)-2-cyclopenten-1-oneYield 50%

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(2-tetrahydropyranyloxy)hexanal (23.2 g., 0.116 mole) and 1-morphdinocyclopentene (25.5 g., 0.16 mole) in benzene (30 ml.) was heated under reflux for 12 hours under nitrogen, and the water liberated was continuously removed with a Dean and Stark head. Benzene (12 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 (84 ml.) and butanol (350 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-(6-hydroxyhexyl)-2-cyclopenten-1-one (10.7 g., 50%), b.p. 105°-160°C./15 mm.Hg, nD25 1.491.

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 (12 ml.) and then, dropwise, 18% hydrochloric acid (28 ml.) were added
  5. customThe organic layer was separated
  6. customevaporated
  7. additionConcentrated hydrochloric acid (84 ml.) and butanol (350 ml.) were 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-602b766d78a24f4bafbfcca6dd7301ba
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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