Hydrochloric Acid → 7-[2-(4-Methyl-3-oxooct-1-enyl)-5-oxocyclopentyl]heptanol

HRID 2286063Notes

Reaction equation

HRID 2286063 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:17]([CH:18]=[CH:19][C:20](=[O:27])[CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][C:10]21OCC[O:11]2.Cl>>[CH3:26][CH:21]([CH2:22][CH2:23][CH2:24][CH3:25])[C:20](=[O:27])[CH:19]=[CH:18][CH:17]1[CH2:16][CH2:15][C:10](=[O:11])[CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 570760486-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

Product 1

HCID 570939037-[2-(4-Methyl-3-oxooct-1-enyl)-5-oxocyclopentyl]heptanolYield 43%

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(7-hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane (1.0 g.) and hydrochloric acid (25 ml; 1 N) was stirred at 60° C. for 2 hours, cooled to ambient temperature and extracted with diethyl ether. The ether extract was washed with 2 N aqueous sodium carbonate solution and water respectively, then dried over magnesium sulphate. Removal of the solvent under reduced pressure gave a crude product (0.7 g.) which was purified by preparative thin layer chromatography on silica gel, using a mixture of diethyl ether, ethyl acetate and hexane (2:1:1 v/v) as eluant, to give 7-[2-(4-methyl-3-oxooct-1-enyl)-5-oxocyclopentyl]heptanol (0.38 g.), νmax (liquid film) 3450 cm-1, 1730 cm-1, 1690 cm-1, 1660 cm-1, 1380 cm-1, 995 cm-1 ; λmax. (ethanol) 230 nm (ε=13,600); Elemental analysis: Found: C, 74.9; H 11.0%; C21H36O3 requires C, 74.95; H, 10.8%; N.M.R. (approximately 10% solution in deuterochloroform): Triplets at 3.57 δ (J=6 cycles/sec.) and 0.88 δ, doublet of doublets at 6.81 δ (J=15.5 cycles/sec. and J=7 cycles/sec.), doublets at 6.20 δ (J=15.5 cycles/sec.) and 1.11 δ (J=7 cycles/sec.), broad singlet 2.0 δ.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with diethyl ether
  3. extractionThe ether extract
  4. washwas washed with 2 N aqueous sodium carbonate solution and water respectively
  5. dry with materialdried over magnesium sulphate
  6. customRemoval of the solvent under reduced pressure
  7. customgave a crude product (0.7 g.) which
  8. customwas purified by preparative thin layer chromatography on silica gel
  9. additiona mixture of diethyl ether, ethyl acetate and hexane (2:1:1 v/v) as eluant

Sources & evidence

ORD record
ord-539e59d5ea1b4fa5999ccb235509e1da
Source dataset
uspto-grants-1982_04
Patent number
US04325967

Reaction notes

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