Lithium diisopropylamide → 4-(4-Methylphenyl)phenol

HRID 1018971Notes

Reaction equation

HRID 1018971 reaction equation
[Li+].CC([N-]C(C)C)C.COP(O)([O:13][CH3:14])=O.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27]C=[CH:25][CH:24]=2)=[CH:19][CH:18]=1>C1COCC1>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][C:14]([OH:13])=[CH:27][CH:28]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 70014764HCID 70014764, compound

Product 1

HCID 13827894-(4-Methylphenyl)phenolYield 33.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of LDA [prepared from diisopropylamine (3.5 mL, 24.5 mmol) and 2.2M n-butyllithium in hexanes (12 mL, 26.4 mmol)] in THF (120 mL) at −78° C. was added a solution of 4′-methyl-biphenyl dimethyl phosphate (6.1 g, 20.9 mmol) in THF (20 mL). The mixture was stirred at −78° C. for 1 h and then at r.t. for 1 h. After quenching with 2M aqueous HOAc (10 mL), solvent was removed in vacuo. The residue was diluted with H2O and extracted with EtOAc. The EtOAc extract was washed with H2O (2×), dried (MgSO4) and concentrated. Chromatography over silica gel and elution with hexanes:EtOAc (3:2) provided 1.3 g of 4′-methyl-4-hydroxybiphenyl. Further elution gave 4.0 g (65.5%) of the title compound as a white solid.

Workup

  1. waitat r.t. for 1 h
  2. customAfter quenching with 2M aqueous HOAc (10 mL), solvent
  3. customwas removed in vacuo
  4. additionThe residue was diluted with H2O
  5. extractionextracted with EtOAc
  6. extractionThe EtOAc extract
  7. washwas washed with H2O (2×)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. washChromatography over silica gel and elution with hexanes:EtOAc (3:2)

Sources & evidence

ORD record
ord-258be1eb25084e9488d924499e392bef
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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