Sodium Hydroxide → 6-Methylsalicylic Acid

HRID 661844

반응식

HRID 661844 반응식
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>CO>[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 584222Ethyl 2-hydroxy-6-methylbenzoate

생성물 1

HCID 112796-Methylsalicylic Acid수율 94.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Step 1 A solution of ethyl 2-hydroxy-6-methylbenzoate (2.04 g, 11.32 mmol) in methanol (25 mL) was treated at rt with 1 M aqueous sodium hydroxide (45.3 mL, 45.3 mmol) and the mixture was heated at reflux for 6 h. The mixture was cooled to rt and the methanol was removed under vacuum. The aqueous residue was treated with 1 M hydrochloric acid to pH ca. 1. The precipitate was collected by filtration, washed with water and dried under vacuum to give 2-hydroxy-6-methylbenzoic acid as a white solid (1.62 g, 94%). 1H NMR (400 MHz, methanol-d4) δ 7.26 (1H, t, J=7.92 Hz), 6.75 (2H, t, J=7.92 Hz), 2.55 (3H, s). Mass spectrum m/z 153.1 (M+H)+.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 h
  3. customthe methanol was removed under vacuum
  4. additionThe aqueous residue was treated with 1 M hydrochloric acid to pH ca. 1
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-709b799f5b24458fb9a3771a4f98b731
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

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