Bromide ion → Benzyl 4-(hydroxymethyl)benzoate

HRID 217637

反応式

HRID 217637 の反応式
[Br-].OC[C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=O)=[CH:6][CH:5]=1.[C:13](=[O:16])([O-])[O-:14].[Cs+].[Cs+].CN([CH:22]=[O:23])C>C(OCC)(=O)C.O.CO>[CH2:8]([O:14][C:13](=[O:16])[C:4]1[CH:12]=[CH:11][C:7]([CH2:22][OH:23])=[CH:6][CH:5]=1)[C:7]1[CH:6]=[CH:5][CH:4]=[CH:12][CH:11]=1

参加物

8

反応物 4

HCID 259Bromide ionHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 763604-(Hydroxymethyl)benzoic acid

生成物 1

HCID 15650225Benzyl 4-(hydroxymethyl)benzoate収率 81%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Benzy bromide (7.8 mL, 66 mmol) was added to a suspension of 4-hydroxymethylbenzoic acid (10 g, 66 mmol) and cesium carbonate (11 g, 34 mmol) in mixed solvent (DMF 0.10 L-methanol 30 mL-water 30 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Water (0.50 L) and ethyl acetate (0.50 L) were added to the reaction solution, and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (0.30 L) and water (0.30 L) twice, respectively. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained solid was filtered and dried at 35° C. under reduced pressure to give 13 g of the title reference compound as a white solid. (Yield 81%)

後処理

  1. customthe mixture was partitioned
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (0.30 L) and water (0.30 L) twice
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. filtrationThe obtained solid was filtered
  6. customdried at 35° C. under reduced pressure
  7. customto give 13 g of the title reference compound as a white solid

出典と根拠

ORDレコード
ord-a3f5334dbc1b4b099c712670860c9367
出典データセット
uspto-grants-2012_06
特許番号
US08198271B2

関連ノート

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