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

HRID 2390860노트

반응식

HRID 2390860 반응식
[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]

참가 물질

3

반응물 1

HCID 127397584-tert-Butyl-3-methoxybenzoic acid

생성물 1

HCID 534014571206775-43-0수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-545d5adc349e4986b53e22395f7aa723
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273773B2

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