Benzyl Bromide → Dimethyl 5-bentyloxy-isophthalate

HRID 658241ノート

反応式

HRID 658241 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

生成物 1

HCID 7643390Dimethyl 5-bentyloxy-isophthalate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of dimethyl 5-hydroxyisophthalate (1 eq.) in DMF (0.5 M) at 0° C. was added portionwise NaH (1.2 eq.) and stirred for 30 min at 0° C. Benzyl bromide (1.2 eq.) was added and the reaction was stirred at rt for 1.5 h. The reaction was then quenched with water ( 1/7 volume), and the resulting precipitate was filtered and washed with hexane. The filtrate was diluted with ether and washed several times with water and brine. The organic extract was dried over MgSO4 and concentrated in vacuo to give a solid which was combined with the filtered precipitate to give dimethyl 5-(benzyloxy)isophthalate. This compound was subsequently dissolved in THF/MeOH (2:1, 0.5 M), and to this solution was added KOH powder. After stirring for 18 h at rt, the reaction was poured into a solution of ether/water. The two layers were separated and the ethereal layer was discarded. The aqueous layer was acidified to pH <1 with 3 N HCl and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid.

後処理

  1. stirringthe reaction was stirred at rt for 1.5 h
  2. customThe reaction was then quenched with water ( 1/7 volume)
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with hexane
  5. additionThe filtrate was diluted with ether
  6. washwashed several times with water and brine
  7. extractionThe organic extract
  8. dry with materialwas dried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a solid which

出典と根拠

ORDレコード
ord-d392c2c1c764419987a48e8ec7777d9b
出典データセット
uspto-grants-2011_12
特許番号
US08076359B2

反応ノート

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