Hydrochloric Acid → 4-(4-Fluorophenyl)-4-hydroxycyclohexan-1-one

HRID 2364103Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:18])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:18])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (1.95 g, 7.73 mmol) in THF (30 mL) was added 3 M HCl (10 mL). The mixture was stirred at 50° C. for 1.5 h, and then poured into EtOAc (50 mL) and aqueous NaHCO3 (50 mL). The aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were washed with brine (15 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to 60:40 hexane/EtOAc) to give the title compound (1.34 g, 83%) as a colorless solid:

Workup

extractionThe aqueous layer was extracted with EtOAc (20 mL)
washThe combined organic layers were washed with brine (15 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (Purif, silica gel, hexane to 60:40 hexane/EtOAc)

Sources & evidence

ORD record: ord-cb8ed5d225244702a6834ed9a094322c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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