Methanol → Dimethyl 2,5-dimethylbenzene-1,4-dicarboxylate

HRID 906132노트

반응식

HRID 906132 반응식
[CH3:1][C:2]1[CH:10]=[C:9](C(O)=O)[C:8]([CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:15][OH:16].[CH3:17][Si](C=[N+]=[N-])(C)C.C[CH2:25][O:26]CC>>[CH3:14][C:8]1[CH:7]=[C:3]([C:4]([O:6][CH3:17])=[O:5])[C:2]([CH3:1])=[CH:10][C:9]=1[C:15]([O:26][CH3:25])=[O:16]

참가 물질

5

반응물 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 2999892,5-Dimethylterephthalic Acid

생성물 1

HCID 289462Dimethyl 2,5-dimethylbenzene-1,4-dicarboxylate수율 93%

실험 절차

2,5-Dimethylterephthalic acid (3 g, 15.5 mmol) was suspended in ether (30 mL) and methanol (10 mL) and was cooled in an ice bath. (Trimethylsilyl)diazomethane (2 M solution in hexanes; 16 mL) was added drop-wise. The mixture was stirred at ambient temperature for 0.5 h and then was quenched with acetic acid (2 mL) and was concentrated. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic portion was washed with brine, dried over sodium sulfate, then filtered and was concentrated to afford dimethyl 2,5-dimethylterephthalate (3.18 g, 14.3 mmol, 93% yield). 1H NMR (400 MHz, CDCl3): δ 7.76 (s, 2H), 3.91 (s, 6H), 2.57 (s, 6H); MS (EI) for C12H14O4: 223 (MH+).

후처리

  1. customwas quenched with acetic acid (2 mL)
  2. concentrationwas concentrated
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe organic portion was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-a8399a0c791c41c987a3fc1f4ce2cf9a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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