Hydrochloric Acid → 2-Hydroxy-5-nitrobenzyl alcohol

HRID 32322

反応式

HRID 32322 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 668085-NitrosalicylaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 27638232-Hydroxy-5-nitrobenzyl alcohol収率 100.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 14798Sodium Hydroxide溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c8e42d1df607468b897faae336df3317
出典データセット
uspto-grants-2008_09
特許番号
US07427608B2

関連ノート

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