Methanol → 4-Bromo-2,6-dimethylbenzoic acid

HRID 2427487

反応式

HRID 2427487 の反応式
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#N)=[C:4]([CH3:11])[CH:3]=1.[OH-:12].[Na+].C[OH:15]>>[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]([OH:15])=[O:12])=[C:4]([CH3:11])[CH:3]=1

参加物

4

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 109107954-Bromo-2,6-dimethylbenzonitrile

生成物 1

HCID 119590064-Bromo-2,6-dimethylbenzoic acid

実験手順

4-Bromo-2,6-dimethylbenzonitrile (4.0 g, 19 mmol) was stirred in MeOH (100 mL) and 5N NaOH (100 mL) at 100° C. for 12 hours. The reaction was cooled to room temperature and partitioned between CH2Cl2 and water and the organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the resulting product was stirred in H2PO3 (20 mL) for 6 hours at 150° C. The reaction mixture was basified with 6M KOH, filtered and then acidified with 12M HCl. The reaction was partitioned between CH2Cl2 and water and the organic layer was dried over anhydrous Na2-SO4. The solvent was removed under reduced pressure to afford the product (2.81 g). 1H NMR (300 MHz, CDCl3): δ 7.22 (s, 2H), 6.17 (s, 1H), 5.67 (s, 1H), 2.36 (s, 6H).

後処理

  1. custompartitioned between CH2Cl2 and water
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. filtrationfiltered
  5. customThe reaction was partitioned between CH2Cl2 and water
  6. dry with materialthe organic layer was dried over anhydrous Na2-SO4
  7. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-a3950c17acdc46008ccc5aa9ae1ac61e
出典データセット
uspto-grants-2011_06
特許番号
US07968570B2

関連ノート

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