2-tert-Butyl-4-methylphenol → HCID 19385684, compound

HRID 2255588Notes

Reaction equation

HRID 2255588 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].C1OCCOCCOCCOCCOCCOC1.Br[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][C:39]([O:41][CH3:42])=[O:40]>CN(C=O)C>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[O:12][CH:38]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:32]=1)[C:39]([O:41][CH3:42])=[O:40])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 170042-tert-Butyl-4-methylphenolHCID 2855718-Crown-6HCID 8063364Methyl 2-(2-bromophenyl)acetate

Product 1

HCID 19385684HCID 19385684, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 1.05 g (9.15 mmol) of a 35% oil dispersion of KH in 15 mL of DMF was added 1.50 g (9.15 mmol) of 2-tert-butyl-4-methylphenol and the mixture was stirred under N2 at room temperature. After 10 minutes, 2.41 g (91.5 mmol) of 18-crown-6 and then a solution of 2.30 g (10.1 mmol) of methyl 2-bromophenylacetate dissolved in 10 mL of DMF were added. The reaction mixture was stirred 17 hours, then partitioned between ethyl acetate and water. The organic layer was separated, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate/hexane to afford 0.750 g (26%) of the title compound.

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred 17 hours
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f9ec212d4b8b4278b35c5ce32435c691
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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