Sodium Hydroxide → 4-(Isobutylsulfonyl)benzoic acid

HRID 1405388ノート

反応式

HRID 1405388 の反応式
[CH2:1]([S:5]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>O1CCOCC1>[CH2:1]([S:5]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 58550723HCID 58550723、化合物

生成物 1

HCID 247087824-(Isobutylsulfonyl)benzoic acid収率 98%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 4-isobutylsulfonylbenzoate (1.00 g, 3.90 mmol), NaOH (10 mL of 1.0 M, 10 mmol), and 1,4-dioxane (10 mL) was heated at 80° C. for 1.5 h. The mixture was cooled to rt before it was concentrated in vacuo. The solid residue was taken up in water and was washed with ethyl acetate which was discarded. The aqueous layer was acidified with 1N HCl and was extracted with ethyl acetate (2×). The combined organics were washed with brine, dried over sodium sulfate, and were concentrated in vacuo. Column chromatography (0-100% ethyl acetate/hexanes) on the residue gave 4-(isobutylsulfonyl)benzoic acid (98%). ESI-MS m/z calc. 242.1, found 243.2 (M+1)+; Retention time: 1.73 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=8.3 Hz, 2H), 8.05 (d, J=8.3 Hz, 2H), 3.03 (d, J=6.5 Hz, 2H), 2.27 (dt, J=13.3, 6.6 Hz, 1H), 1.08 (d, J=6.7 Hz, 6H).

後処理

  1. temperatureThe mixture was cooled to rt before it
  2. concentrationwas concentrated in vacuo
  3. washwas washed with ethyl acetate which
  4. extractionwas extracted with ethyl acetate (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationwere concentrated in vacuo

出典と根拠

ORDレコード
ord-748896b252114cf0ae4b027c32d6db7a
出典データセット
uspto-grants-2014_12
特許番号
US08916565B2

反応ノート

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