Hydrochloric Acid → (2-Chloro-4-methylphenyl)methanol

HRID 2167885

반응식

HRID 2167885 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1.Cl.CCOCC>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 2723981Borane;tetrahydrofuranHCID 27357552-Chloro-4-methylbenzoic acid

생성물 1

HCID 15544016(2-Chloro-4-methylphenyl)methanol수율 89.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

as follows: To a solution of 2-chloro-4-methylbenzoic acid (2.18 g; 12.8 mmol) in THF (22 mL) was added dropwise a solution of BH3.THF in THF (25.6 ml; 1.00 mol/l; 25.6 mmol), at 0° C. Upon complete addition the resulting mixture was heated under reflux, for 3 hours. Subsequently, the mixture was cooled to 0° C., 1M aqueous HCl (30 mL) was added dropwise, and the mixture was stirred for 10 min. Et2O (100 mL) was added and the layers were separated. The organic layer was washed with 1M aqueous HCl (2×), 5% aqueous NaHCO3 (2×), and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford (2-chloro-4-methyl-phenyl)-methanol (1.80 g), which was used as such.

후처리

  1. customat 0° C
  2. additionUpon complete addition the resulting mixture
  3. temperaturewas heated
  4. temperatureunder reflux, for 3 hours
  5. customthe layers were separated
  6. washThe organic layer was washed with 1M aqueous HCl (2×), 5% aqueous NaHCO3 (2×), and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-50db0fbaaa8e4b968395e9a42dc1411a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045441B2

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