Hydrochloric Acid → 1-(2-Hydroxy-3,5-diisopropylphenyl)ethanone

HRID 1272266Notes

Reaction equation

HRID 1272266 reaction equation
C[Mg]Br.C([O:6][CH2:7][CH3:8])C.[OH:9][C:10]1[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][C:15]([CH:21]([CH3:23])[CH3:22])=[CH:14][C:11]=1C#N.Cl>O.C1COCC1>[OH:9][C:10]1[C:17]([CH:18]([CH3:19])[CH3:20])=[CH:16][C:15]([CH:21]([CH3:23])[CH3:22])=[CH:14][C:11]=1[C:7](=[O:6])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 184569012-Hydroxy-3,5-diisopropyl benzonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 109769901-(2-Hydroxy-3,5-diisopropylphenyl)ethanoneYield 12.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To dry THF (10 mL) there was added 3.0 M solution of methylmagnesium bromide in diethylether (Aldrich) (10.9 mL; 32.8 mmole) and then a previously prepared solution of 2-hydroxy-3,5-diisopropyl benzonitrile (2.78 g, 13.7 mmole) and dry THF (70 mL) was added. After 7 hours under the reflux the reaction mixture was mixed with water (100 mL), acidified with concentrated hydrochloric acid (50 mL) and refluxed for one more hour. After cooling and extraction with ethyl acetate an oily product was obtained, which was purified on a silica gel column, whereat there were obtained 380 mg (12.5%) of 2′-hydroxy-3′5′-diisopropylacetophenone:

Workup

  1. temperatureAfter 7 hours under the reflux the reaction mixture
  2. temperaturerefluxed for one more hour
  3. temperatureAfter cooling
  4. extractionextraction with ethyl acetate an oily product
  5. customwas obtained
  6. customwhich was purified on a silica gel column, whereat there

Sources & evidence

ORD record
ord-2099cba3de84451998fe6e6200b1115b
Source dataset
uspto-grants-2007_04
Patent number
US07208518B2

Reaction notes

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