Acetone → 4-(4-Bromophenyl)-4-(hydroxymethyl)cyclohexanone

HRID 881715Notes

Reaction equation

HRID 881715 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][OH:19])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CC(C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:18][OH:19])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 86700821(8-(4-Bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol

Product 1

HCID 867008224-(4-Bromophenyl)-4-(hydroxymethyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a round bottom flask containing (8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol (4.88 g, 14.91 mmol) was added acetone (34 ml) and water (17 ml) at room temperature. p-toluenesulfonic acid (57 mg, 0.30 mmol) was then added and the mixture heated to 75° C. for 1 hour. The content was cooled to room temperature and concentrated under reduced pressure to remove the excess acetone. The resulting aqueous mixture was extracted with EtOAc twice. The combined organic portion was dried over sodium sulfate and concentrated to afford the title compound as white solid. (4.22 g) LC/MS, ESI-MS: non-ionizable, RT: 1.05 (Condition E).

Workup

  1. temperatureThe content was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto remove the excess acetone
  4. extractionThe resulting aqueous mixture was extracted with EtOAc twice
  5. dry with materialThe combined organic portion was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d4444943df3f45658a5a70260f84b787
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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