Hydrochloric Acid → 4-Hydroxy-4-(4-iodophenyl)cyclohexanone

HRID 1016061Notes

Reaction equation

HRID 1016061 reaction equation
[I: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.[OH-].[Na+]>CC(C)=O>[OH:18][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 578033098-(4-Iodo-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol

Product 1

HCID 595561854-Hydroxy-4-(4-iodophenyl)cyclohexanoneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 8-(4-iodo-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol (2 g) in acetone (10 mL) was added 5% HCl (20 mL) and the mixture was stirred at rt for 14 hours. The mixture was neutralized with 1N NaOH to pH 7, concentrated on rotovap, and then extracted with ethyl acetate (2×50 mL). The organic extracts were combined, washed with saline solution (2×50 mL), dried over sodium sulfate, concentrated in vacuo to provide 4-hydroxy-4-(4-iodophenyl)cyclohexanone (1.7 g, 98%). LCMS: 317.3 (M+H+, 100%).

Workup

  1. concentrationconcentrated on rotovap
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washwashed with saline solution (2×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1404de6a0f0943dab933c47574c8ec73
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

Loading…