Diethyl Ether → HCID 20517423, compound

Participants

Reaction Steps

To a freshly prepared solution of diazoethane in ether (~550 ml of 0.297 M=163 mmol) cooled to -10° C. and well stirred with a magnetic stirrer in an open 1 liter Erlenmeyer flask is added slowly a solution of 4-hydroxycyclohexanone (14.8 g, 13 mmol) in ethanol (150 ml) over a period of 15 minutes. The cooling bath is removed and the stirred reaction mixture is allowed to come to room temperature and stirred overnight. The excess diazoethane is discharged by adding a few drops of 10% aq. acetic acid and then the solvent is removed in vacuo. The residue is dissolved in ether, washed with a satd. aq. NaHCO3 solution, dried (Na2SO4) and the ether is removed in vacuo. Distillation of the residue in vacuo affords (±) 5-hydroxy-2-methylcycloheptanone which exists as an equilibrium mixture with its tautomeric bicyclic hemiacetal form (bp, 1.4 mm, 97°-99°, 17.51 g, 95%). IR (neat)μ: 2.93 (OH), 5.90 (C=O); NMR (CDCl3)δ: 0.91 (d, J=7 Hz, 2-CH of 2-y), 1.08 (d, J=7 Hz, 2--CH3), 3.4-4.5 (m, H--C<--OH and H--C<--O--C); GC-MS: RGC shows two components (~60:40) both of which show M+ 142 and identical fragmentations. MOX derivatization gave a single peak in RGC with M+ 171.

Provenance & Evidence