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Bromide ion → Benzyl 4-(hydroxymethyl)benzoate

HRID 217637
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HRID 217637 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

HCID 15650225Benzyl 4-(hydroxymethyl)benzoate수율 81%

시약·촉매·용매 3

HCID 887Methanol용매
HCID 962
Water
용매
2회
HCID 8857Ethyl Acetate용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-a3f5334dbc1b4b099c712670860c9367
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08198271B2

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