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

HRID 906092노트

반응식

HRID 906092 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 117888183,4-Dimethoxy-2-methylbenzoic acid수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-81dfe62ff2c04032b87700d7fbfd9e89
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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