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

HRID 2390860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390860
[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]

Komponenten

3

Edukt 1

HCID 127397584-tert-Butyl-3-methoxybenzoic acid

Produkt 1

HCID 534014571206775-43-0Ausbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-545d5adc349e4986b53e22395f7aa723
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273773B2

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