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

HRID 906132ノート

反応式

HRID 906132 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-a8399a0c791c41c987a3fc1f4ce2cf9a
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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