Sulfuric Acid → 7-(Oxan-2-yloxy)heptanal

HRID 1581097Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#N.S(=O)(=O)(O)[OH:27]>C1C=CC=CC=1.C(OCC)C>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[O:27]

Participants

Conditions

Temperature: 10 °C

Procedure

Diisobutylaluminium hydride (19.4 g., 0.14 mole) in dry benzene (50 ml.) was added dropwise at 10°C. to a stirred solution of 7-(2-tetrahydropyranyloxy)heptanenitrile (20.6 g., 0.1 mole) in dry diethyl ether (200 ml.). The solution was stirred at 10°C. for 30 minutes and was then added to 2N aqueous sulphuric acid (300 ml.) at 0°C. The mixture was heated at 30°C. for 30 minutes, and then saturated with sodium chloride and the layers were separated. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with aqueous sodium bicarbonate, and then aqueous sodium chloride, and dried over sodium sulphate. The solvent was evaporated and the residue was distilled under reduced pressure to give 7-(2-tetrahydropyranyloxy)heptanal (12.7 g., 66%), b.p. 78°-106°C./0.1 mm.Hg, nD25 1.456.

Workup

temperatureThe mixture was heated at 30°C. for 30 minutes
customsaturated with sodium chloride and the layers were separated
extractionThe aqueous layer was extracted with diethyl ether
washthe combined organic layers were washed with aqueous sodium bicarbonate
dry with materialaqueous sodium chloride, and dried over sodium sulphate
customThe solvent was evaporated
distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record: ord-61835a8ba825486680a15f3fa92216e7
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03935261

Reaction notes

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