Sodium Bicarbonate → 4-(1-Hydroxy-4-oxocyclohexyl)benzonitrile

HRID 1015980Notes

Reaction equation

[OH:1][C:2]1([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.C([O-])(O)=O.[Na+].C(OCC)(=O)C.CCCCCC>C1COCC1.Cl>[OH:1][C:2]1([C:12]2[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=2)[CH2:3][CH2:4][C:5](=[O:6])[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

4-(8-Hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)benzonitrile (520 mg, 2.0 mmol) was dissolved in the mixed solvent of 10 mL of THF and 10 mL of 1 N HCl aqueous solution at room temperature. The reaction mixture was then stirred at 60° C. for 1 h. The solution was cooled down to room temperature, adjusted to pH 7-8 with saturated NaHCO3 aqueous solution. The organic layer was separated, and the aqueous layer was extracted twice with EtOAc (20 mL×2). The combined organic extracts were dried over MgSO4 and evaporated to give an oil residue. Chromatography on silica gel (flash chromatography grade) with 40% ethyl acetate-hexane gave 410 mg (95%) of the desired product: 1H NMR (CDCl3) δ 7.7 (2H, d, J=11.0 Hz), 7.42 (2H, d, J=10.7 Hz), 4.10 (H, s), 2.79-2.74 (2H, m), 2.63-2.49 (2H, m), 1.95-1.89 (2H, m), 1.67-1.59 (2H, m); MS: 216 (M+1)+.

Workup

temperatureThe solution was cooled down to room temperature
customThe organic layer was separated
extractionthe aqueous layer was extracted twice with EtOAc (20 mL×2)
dry with materialThe combined organic extracts were dried over MgSO4
customevaporated
customto give an oil residue

Sources & evidence

ORD record: ord-6bf26003771a42aca5c9e1274e084b21
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985730B2

Reaction notes

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