Hydrochloric Acid → 2-Hydroxy-5-nitrobenzyl alcohol

HRID 32322

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HRID 32322 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>[OH-].[Na+].CO>[OH:5][CH2:4][C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[OH:1]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 668085-NitrosalicylaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 27638232-Hydroxy-5-nitrobenzyl alcohol수율 100.5%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 14798Sodium Hydroxide용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 2-hydroxy-5-nitrobenzaldehyde (5.01 g, 30 mmol) in a mixture of 60 mL 1M NaOH and 30 mL MeOH was cooled to 0° C. NaBH4 (1.13 g, 30 mmol) solution in 15 ml 1M NaOH and 5 mL MeOH was added slowly. The reaction mixture was stirred for 24 hours at room temperature. The mixture was poured into ice cooled 2M HCl and extracted with EtOAc. The organic layer was washed, dried, and evaporated in vacuo to give the alcohol as a yellow solid (5.1 g, 100%): MP 112-114° C.; 1H NMR (DMSO-d6, 400 MHz) δ 11.08 (s, 1H), 8.18 (d, 1H, J=2.5 Hz), 8.00 (dd, 1H, J=2.5 and 8.7 Hz), 6.92 (d, 1H, J=8.8 Hz), 5.20 (br, 1H), 4.49 (s, 2H).

후처리

  1. additionThe mixture was poured into ice
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed
  4. customdried
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-c8e42d1df607468b897faae336df3317
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427608B2

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