Hydrochloric Acid → HCID 86652996, compound

HRID 1186042Notes

Reaction equation

HRID 1186042 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].Cl>C(Cl)Cl.CO.O>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:5](=[O:7])[CH3:6])=[CH:15][C:14]=1[OH:19])([CH3:12])([CH3:10])[CH3:11]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 69232-Tert-ButylphenolHCID 11430Potassium CarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86652996HCID 86652996, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of aluminum chloride (162.3 g, 1.22 mol) in methylene chloride (600 mL) at −75° C. was added acetyl chloride (95.7 g, 1.22 mol) while stirring under an atmosphere of argon. 2-tert-Butyl-phenol (167 g, 1.11 mol) was added dropwise over 1 hr. The resulting mixture was allowed to warm to 0° C. for 10 min. The resulting mixture was then quenched with ice and extracted with EtOAc (1.5 L). The organic layer was separated and dried with brine. The organic layer was evaporated in vacuo to yield a white solid. The white solid was dissolved in methanol (300 mL) and treated with potassium carbonate (100 g) and the resulting mixture allowed to stir 18 h at room temperature. Water (300 mL) was added and pH adjusted to 5 to 6 using concentrated hydrochloric acid. The resulting mixture was extracted with EtOAc. The organic layer was rinsed with brine and dried over sodium sulfate, then evaporated in vacuo to yield 1-(4-tert-butyl-3-hydroxy-phenyl)-ethanone as a tan solid. C12H16O2; MS (ESI) m/z 193.2 (MH)+.

Workup

  1. customThe resulting mixture was then quenched with ice
  2. extractionextracted with EtOAc (1.5 L)
  3. customThe organic layer was separated
  4. dry with materialdried with brine
  5. customThe organic layer was evaporated in vacuo
  6. customto yield a white solid
  7. stirringto stir 18 h at room temperature
  8. extractionThe resulting mixture was extracted with EtOAc
  9. washThe organic layer was rinsed with brine
  10. dry with materialdried over sodium sulfate
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-7caa68145e19460db9afe470d42512bd
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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