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

HRID 1858930Notes

Reaction equation

HRID 1858930 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>CO>[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 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (8.6 g, 36 mmole) in a mixture of 50% aqueous methanol and concentrated HCl (3 ml) was stirred for 78 hr. The methanol was removed in vacuo without heating and the residue extracted with ether. The extracts were dried with Na2SO4 and the solvent removed in vacuo to give the product (6.0 g, 86%, mp: 118-119° C.). Calc'd for C12H13FO2 : C, 69.22%; H, 6.30%. Found: C, 69.32%; H, 6.34%.

Workup

  1. customThe methanol was removed in vacuo
  2. temperaturewithout heating
  3. extractionthe residue extracted with ether
  4. dry with materialThe extracts were dried with Na2SO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cd6d977fa70e4f1aa263aa3f1fd9328b
Source dataset
uspto-grants-2000_11
Patent number
US06153611

Reaction notes

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