2-Methyl-2-butene → 4-Bromo-2-methoxy-6-methylbenzoic acid

HRID 515160ノート

反応式

HRID 515160 の反応式
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.Cl([O-])=[O:14].[Na+].P(O)(O)([O-])=O.[Na+].CC(=CC)C>C(O)(C)(C)C.O>[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]([OH:14])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

参加物

7

反応物 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 454803854-Bromo-2-methoxy-6-methylbenzaldehyde

生成物 1

HCID 454803864-Bromo-2-methoxy-6-methylbenzoic acid収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

To a suspension of 4-bromo-2-methoxy-6-methyl-benzaldehyde (1.25 g, 5.45 mmol) in tert-butanol (21.7 ml) is added a solution of sodium chlorite (0.98 g, 10.9 mmol) and monosodium phosphate (4.25 g, 27.3 mmol) in water (11 ml). To the solution is added 2-methyl-2-butene (4.63 ml, 43.7 mmol). The resulting homogeneous solution is stirred at RT for 30 min. After completion of the reaction, the solvent is evaporated and the residue is diluted with water and acidified with 1 M hydrochloric acid to pH=1 and extracted with methyl tert-butyl ether (3×40 ml). The combined organic layers are extracted with 1 M sodium hydroxide solution which is further acidified with 6 M hydrochloric acid and extracted with ethyl acetate (3×50 ml). The organic layer is washed with brine (40 ml), dried over sodium sulfate and concentrated to yield 4-bromo-2-methoxy-6-methyl-benzoic acid (1.2 g, 4.89 mmol, 90%).

後処理

  1. customAfter completion of the reaction
  2. customthe solvent is evaporated
  3. additionthe residue is diluted with water
  4. extractionextracted with methyl tert-butyl ether (3×40 ml)
  5. extractionThe combined organic layers are extracted with 1 M sodium hydroxide solution which
  6. extractionextracted with ethyl acetate (3×50 ml)
  7. washThe organic layer is washed with brine (40 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-59d2fc30d3cf4f7698d9e9e835731d24
出典データセット
uspto-grants-2015_08
特許番号
US09108936B2

反応ノート

読み込み中…