6-(7-Hydroxyheptyl)-7-(3-hydroxy-4-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane → 7-[2-(3-Hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanol

HRID 372052Notes

Reaction equation

HRID 372052 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][CH:20]([OH:27])[CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][C:10]21OCC[O:11]2>Cl>[OH:27][CH:20]([CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[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 1

HCID 570090666-(7-Hydroxyheptyl)-7-(3-hydroxy-4-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane

Product 1

HCID 542676867-[2-(3-Hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanolYield 33.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of crude 6-(7-hydroxyheptyl)-7-(3-hydroxy-4-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane (0.5 g.) and hydrochloric acid (50 ml; 2N) was stirred at 60° C. for 2 hours, cooled to ambient temperature and then extracted with diethyl ether. The ether extract was washed with water and dried over magnesium sulphate. Removal of the solvent under reduced pressure gave a crude product (0.4 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-(3-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl]heptanol (0.15 g.), νmax 3400 cm-1, 1725 cm-1, 970 cm-1 ; Elemental analysis: Found C, 74.8; H, 11.7%; C21H38O3 requires C, 74.5; H, 11.53%; N.M.R. (approximately 10% solution in deuterochloroform): multiplets at 5.7-5.5 δ, 3.98 δ and 1.05-0.7 δ, triplet at 3.6 δ (J = 6 cycles/sec.), based singlet at 2.05 δ.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with diethyl ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulphate
  6. customRemoval of the solvent under reduced pressure
  7. customgave a crude product (0.4 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-129da0f9e9194acca766a9bc38bb44d0
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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