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

HRID 906084노트

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HRID 906084 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 232121724-(Hydroxymethyl)-2-methylbenzoic acid수율 76%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
25 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-9a603f01e4b94270871c2d7e680f3030
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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