Water → HCID 89543041、化合物

HRID 2204234ノート

反応式

HRID 2204234 の反応式
[C:1]([S:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH:16]OS([O-])=O.[K+]>CO>[C:1]([S:5]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 962WaterHCID 222172344-[(1,1-Dimethylethyl)thio]benzoic acidHCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 89543041HCID 89543041、化合物収率 156.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-(tert-Butylthio)benzoic acid (3.18 g, 15.1 mmol) was dissolved in methanol (78.70 mL) followed by the addition of water (7.9 mL) and OXONE (4.65 g, 7.56 mmol). The reaction mixture was stirred at room temperature for 45 minutes before it was filtered using methanol. The solvent was evaporated under reduced pressure. Water (35 mL) was added to the residue and the mixture was basified using solid NaOH and was washed with ethyl acetate (3×50 mL). The aqueous layer was acidified with 1N HCl before it was extracted with ethyl acetate (3×100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 4-(tert-butylsulfinyl)benzoic acid (2.68 g, 78%) as a white solid. 1H NMR (400 MHz, DMSO) δ 13.29 (s, 1H), 8.12-8.08 (m, 2H), 7.73-7.69 (m, 2H), 1.09 (s, 9H). ESI-MS m/z calc. 226.1, found 227.3 (M+1)+; Retention time: 1.05 minutes (3 min run).

後処理

  1. filtrationwas filtered
  2. customThe solvent was evaporated under reduced pressure
  3. additionWater (35 mL) was added to the residue
  4. washwas washed with ethyl acetate (3×50 mL)
  5. extractionwas extracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bb877fcb0da74c47985ca22e401ddbd7
出典データセット
uspto-grants-2016_06
特許番号
US09365588B2

反応ノート

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