Ethyl Acetate → 1-(2-Hydroxyphenyl)-2-methylpropan-1-one

HRID 1528164Notes

Reaction equation

HRID 1528164 reaction equation
[CH:1]([Li])([CH2:3][CH3:4])C.C([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1Br)(=O)C(C)C.[C:19](OCC)(=[O:21])C.C(=O)(O)O.[Na]>C1CCCCC1.O1CCCC1>[OH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:19](=[O:21])[CH:3]([CH3:1])[CH3:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 13697103HCID 13697103, compoundHCID 24192197Carbonic acid, sodium saltHCID 178418400CID 53628100

Product 1

HCID 2415551-(2-Hydroxyphenyl)-2-methylpropan-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-75 °C

Procedure

100 ml of sec-butyllithium at 1.4 M in cyclohexane were added dropwise to a solution of 31.59 g (130 mmol) of 2-bromophenyl isobutyrate in 300 ml of tetrahydrofuran at −85° C. under nitrogen. The reaction medium was maintained for 30 minutes at approximately −75° C. and was then left to gently return to ambient temperature. After 2 hours, a little ethyl acetate was added, followed by approximately 400 ml of a 1 M aqueous sodium dihydrogen carbonate solution. The organic phase was recovered, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated. 23.97 g of an orange oil were obtained and purified on silica cake. The residue obtained was chromatographed on a prepacked silica column (eluent heptane/ethyl acetate). 4.3 g of product were obtained in the form of a yellow oil. Yield=20%.

Workup

  1. waitwas then left
  2. customto gently return to ambient temperature
  3. customThe organic phase was recovered
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-35ceb2dd48c241e8b4146268d553cad6
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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