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

HRID 372050Notes

Reaction equation

HRID 372050 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; 1N) was stirred at 60° C. for 2 hours, cooled to ambient temperature and extracted with diethyl ether. The ether extract was washed with 2N 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 2N 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-35be1f87b90243f7b977b933c873fae1
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

Loading…