Carbon Dioxide → 3,4-Dimethoxy-2-methylbenzoic acid

HRID 906092ノート

反応式

HRID 906092 の反応式
[Mg].Br[C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([O:12][CH3:13])=[CH:5][CH:4]=1.C[Mg]Br.[C:17](=[O:19])=[O:18].Cl>O1CCCC1.O>[CH3:11][O:10][C:7]1[C:8]([CH3:9])=[C:3]([CH:4]=[CH:5][C:6]=1[O:12][CH3:13])[C:17]([OH:19])=[O:18]

参加物

8

反応物 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8259711-Bromo-3,4-dimethoxy-2-methylbenzeneHCID 5462224MagnesiumHCID 178418573HCID 178418573、化合物

生成物 1

HCID 117888183,4-Dimethoxy-2-methylbenzoic acid収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of magnesium turnings (0.059 g, 2.40 mmol) in tetrahydrofuran (1 ml) was added a solution of 6-bromo-2,3-dimethoxy toluene (0.660 g, 2.3 mmol) in tetrahydrofuran (1 ml). The reaction was initiated by addition of methylmagnesium bromide and the solution was stirred at room temperature overnight under nitrogen. To the mixture was then added an excess of dry ice. When the addition was complete, water was added (2 ml) followed by 1.5 M hydrochloric acid to pH 2. The water phase was extracted with ethyl acetate (2×5 ml) and the combined organic layers were dried over sodium sulfate, filtered and concentrated to give 3,4-dimethoxy-2-methylbenzoic acid (0.315 g, 70% yield). MS (EI) for C10H12O4: 195 (M−H).

後処理

  1. additionWhen the addition
  2. extractionThe water phase was extracted with ethyl acetate (2×5 ml)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-81dfe62ff2c04032b87700d7fbfd9e89
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

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