Oxygen → Methyl 4-formyl-2-hydroxybenzoate

HRID 1160792

반응식

HRID 1160792 반응식
[O:1]=O.[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=C)=[CH:8][C:7]=1[OH:14].CSC>C(Cl)Cl>[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:1])=[CH:8][C:7]=1[OH:14]

참가 물질

5

반응물 3

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 200893762-Hydroxy-4-vinyl-benzoic acid methyl ester

생성물 1

HCID 21626741Methyl 4-formyl-2-hydroxybenzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A steady stream of O2 (g) is passed through a cold (−78° C.) solution of 2-hydroxy-4-vinyl-benzoic acid methyl ester (3.28 g, 0.0184 mol) in CH2Cl2 (50 ml). After 5 minutes, O3 (g) is bubbled into the solution until the solution's color turns blue/gray. The solution is then purged with O2 (g) for 5 minutes, treated with DMS (4.05 ml, 0.0552 mol) and allowed to warm to room temperature overnight. All volatiles are removed in vacuo and the crude product is purified with silica gel column chromatography (0-100% ethyl acetate in hexanes gradient) to afford 4-formyl-2-hydroxy-benzoic acid methyl ester: ESMS m/z 181.0 (M+H+).

후처리

  1. customO3 (g) is bubbled into the solution until the solution's color
  2. customThe solution is then purged with O2 (g) for 5 minutes
  3. customAll volatiles are removed in vacuo
  4. customthe crude product is purified with silica gel column chromatography (0-100% ethyl acetate in hexanes gradient)

출처 및 근거

ORD 기록
ord-50dfd616d60b45768fcd576e814a3371
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816542B2

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