Sodium borohydride → 4-(Hydroxymethyl)-2-methylbenzoic acid

HRID 906084ノート

反応式

HRID 906084 の反応式
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 207748714-Formyl-2-methylbenzoic acid

生成物 1

HCID 232121724-(Hydroxymethyl)-2-methylbenzoic acid収率 76%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

To 4-formyl-2-methylbenzoic acid (75 mg, 0.46 mmol), in methanol (5 ml), was added sodium borohydride (26 mg, 0.69 mmol). The solution was stirred at 25° C. for 1 h. The reaction was quenched with saturated aqueous ammonium chloride and the pH adjusted to 2 with 2 N aqueous hydrochloric acid, then extracted with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude 4-(hydroxymethyl)-2-methylbenzoic acid (37 mg, 76%) was obtained and was used without further purification. 1H NMR (400 MHz, DMSO): 12.73-12.68 (s, 1H), 7.82-7.77 (d, 1H), 7.24-7.19 (m, 2H), 5.32-5.27 (m, 1H), 4.53-4.48 (d, 2H), 2.53-2.49 (s, 3H). MS (EI) for C9H10O3: 167 (MH+).

後処理

  1. customThe reaction was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9a603f01e4b94270871c2d7e680f3030
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

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