Sodium sulfate decahydrate → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 1970979Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[C:11]2([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

To LAH (9.11 g, 240 mmol) in THF (100 mL) was added 1,4-dioxaspiro[4.5]decan-8-one (25 g, 160 mmol) in THF (100 mL) dropwise at 0° C. The reaction mixture was left to stir for 30 min at 0° C., and allowed to warm to room temperature. The reaction was monitored by TLC until the ketone was fully converted to the alcohol. The reaction mixture was treated with sodium sulfate decahydrate in small portions, filtered through a pad of Celite, and concentrated to give the title compound.

Workup

waitThe reaction mixture was left
temperatureto warm to room temperature
filtrationfiltered through a pad of Celite
concentrationconcentrated

Sources & evidence

ORD record: ord-95344daaea5f4369993ddc0ba89e48fd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431569B2

Reaction notes

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