Oxygen → Methyl 4-formyl-2-hydroxybenzoate

HRID 1160792ノート

反応式

HRID 1160792 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 21626741Methyl 4-formyl-2-hydroxybenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-50dfd616d60b45768fcd576e814a3371
出典データセット
uspto-grants-2010_10
特許番号
US07816542B2

反応ノート

読み込み中…