(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol → 2,2-Dimethyl-1,3-dioxan-5-one

HRID 931875Notes

Reaction equation

N[C:2]1(CO)[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4][CH2:3]1.[OH:12]P([O-])(O)=O.[K+]>O>[CH3:9][C:5]1([CH3:8])[O:4][CH2:3][C:2](=[O:12])[CH2:7][O:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a water (1.5 L) solution of (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol (251 g, 1.57 mol) and KH2PO4 (213 g, 1.57 mol) at 0° C., a water solution (1.8 L) of NaIO4 (336 g, 1.57 mol) was added dropwise. The reaction mixture was stirred at 0° C. for 2 hours and room temperature overnight. The product was extracted by CH2Cl2 (5×300 mL), dried over MgSO4 and distilled, yielding 2,2-Dimethyl-1,3-dioxan-5-one (153 g, 75%) as a colorless liquid, by 102° C./40 torr. 1H NMR (300 MHz, CDCl3) δ1.26 (s, 6H), 3.96 (s, 4H).

Workup

extractionThe product was extracted by CH2Cl2 (5×300 mL)
dry with materialdried over MgSO4
distillationdistilled

Sources & evidence

ORD record: ord-b9c93474f7564d57870d002f817e2e63
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09298093B2

Reaction notes

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