Sodium Carbonate → 3-Chloro-2-hydroxy-4-methoxybenzoic acid

HRID 629380ノート

反応式

HRID 629380 の反応式
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].P([O-])(O)(O)=[O:14].[Na+].Cl([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.CS(C)=O>[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]([OH:14])=[O:6]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 133437063-Chloro-4-methoxysalicylaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

生成物 1

HCID 847769843-Chloro-2-hydroxy-4-methoxybenzoic acid収率 61.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

反応条件

温度
15 °C

実験手順

To a solution of 3-chloro-2-hydroxy-4-methoxybenzaldehyde (16.6 g) and sodium dihydrogenphosphate (34.7 g) in a mixed solvent of DMSO (180 mL)-water (45.0 mL) was added an aqueous solution (35.0 mL) of sodium chlorite (27.2 g) under ice-cooling, and the mixture was stirred at 15° C. for 16 hr. The reaction mixture was poured into saturated aqueous sodium carbonate solution, the mixture was diluted with water, and filtered, and the filtrate was extracted with petroleum ether/ethyl acetate=5:1. The aqueous layer was acidified with conc. hydrochloric acid to adjusted pH=1, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (11.1 g).

後処理

  1. temperaturecooling
  2. filtrationfiltered
  3. extractionthe filtrate was extracted with petroleum ether/ethyl acetate=5:1
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with 1N hydrochloric acid
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-8cd53e5107f0418493cc58350d19959a
出典データセット
uspto-grants-2016_04
特許番号
US09315458B2

反応ノート

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