Boron trifluoride etherate → 1-(2,4-Dihydroxy-5-isopropylphenyl)ethanone

HRID 2097287Notes

Reaction equation

HRID 2097287 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11])([CH3:3])[CH3:2].B(F)(F)F.[CH3:16][CH2:17][O:18]CC.CC([O-])=O.[Na+]>C(O)(=O)C>[OH:10][C:7]1[CH:6]=[C:5]([OH:11])[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][C:8]=1[C:17](=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 901354-IsopropylresorcinolHCID 517045Sodium Acetate

Product 1

HCID 247733601-(2,4-Dihydroxy-5-isopropylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

4-Isopropyl-benzene-1,3-diol (1 eq) was taken up in BF3.OEt2 (6 eq) and acetic acid was added (2 eq). The solution was heated for 16 hours at 90° C. than allowed to cool to room temperature. The solution was added drop wise to 10% NaOAc (aq) and allowed to stand for 4 hours, before being extracted in to EtOAc. The organic phases were combined and washed with sat. NaHCO3 (aq), then dried over MgSO4, filtered and concentrated in vacuo. The residual oil was purified by column chromatography, eluting with dichloromethane, to give 1-(2,4-Dihydroxy-5-isopropyl-phenyl)-ethanone as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionbefore being extracted in to EtOAc
  3. washwashed with sat. NaHCO3 (aq)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was purified by column chromatography
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-dfe27f9a5fef40b3bccd9485708b9568
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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