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

HRID 1637084Notes

Reaction equation

HRID 1637084 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>O1CCOCC1>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 152326818-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 223953644-(4-Fluorophenyl)-4-hydroxycyclohexan-1-oneYield 79.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 8-(4-fluorophenyl)-1,4-dioxa-spiro[4.5]decan-8-ol (38 g, 0.15 mol) in dioxane (900 ml), cooled to 0° C. was added hydrogen chloride (1M in water, 1.5 L, 1.5 mol). The reaction mixture was stirred for 2 hour at RT and extracted twice with ethyl acetate. The ethyl acetate layer was washed with saturated sodium bicarbonate solution, water and brine. Drying and solvent evaporation gave 4-(4-fluorophenyl)-4-hydroxy-cyclohexanone (24.8 g, 79%); 1H NMR (CDCl3)δ 7.55-7.45 (m, 2H) 7.16-7.0 (m, 2H), 3.0-2.85 (m, 2H), 2.18-2.38 (m, 6H), 1.85 (s, 1H)

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated sodium bicarbonate solution, water and brine
  3. customDrying
  4. customsolvent evaporation

Sources & evidence

ORD record
ord-526d0e90b0e544138724e6ca37d3526d
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

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