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

HRID 1809932Notes

Reaction equation

HRID 1809932 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 rotvap, 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 rotvap
  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-97f8fdf4e9a84a278ecaf0fe4ae74b72
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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