4-tert-Butyl-3-methoxybenzoic acid → 1206775-43-0

HRID 2390860Notes

Reaction equation

HRID 2390860 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 127397584-tert-Butyl-3-methoxybenzoic acid

Product 1

HCID 534014571206775-43-0Yield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

step a—To a solution of 4-tert-butyl-3-methoxybenzoic acid (3.00 g, 14.40 mmol, CASRN 79822-46-1) in THF (60 mL) cooled to 5° C. was added dropwise a solution of BH3-Me2S (2.0M in THF, 16.60 mL, 33.10 mmol). The reaction was allowed to stir for 24 h at RT then cooled to −50° C. and quenched by dropwise addition of MeOH (20 mL). The reaction mixture was warmed to RT and concentrated in vacuo. The residue was taken up in MeOH (3×20 mL) and concentrated in vacuo. The final residue partitioned between EtOAc and sat'd. aq. NaHCO3. The organic layer was washed with water, brine, dried (MgSO4), filtered and concentrated to afford 2.64 g (95%) of (4-tert-Butyl-3-methoxy-phenyl)-methanol (345) as a colorless oil.

Workup

  1. temperaturethen cooled to −50° C.
  2. customquenched by dropwise addition of MeOH (20 mL)
  3. temperatureThe reaction mixture was warmed to RT
  4. concentrationconcentrated in vacuo
  5. concentrationconcentrated in vacuo
  6. customThe final residue partitioned between EtOAc
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-545d5adc349e4986b53e22395f7aa723
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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