Boron trifluoride etherate → 2-Hydroxy-4,5-dimethoxybenzoic acid

HRID 78697

반응식

HRID 78697 반응식
C[O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[Na+].[Br-].B(F)(F)F.CCOCC.[OH-].[Na+]>C(OCC)(=O)C.O>[OH:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

참가 물질

7

반응물 4

HCID 8000Boron trifluoride etherateHCID 102762,4,5-Trimethoxybenzoic acidHCID 14798Sodium HydroxideHCID 253881Sodium Bromide

생성물 1

HCID 115646502-Hydroxy-4,5-dimethoxybenzoic acid수율 91%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
40 °C

실험 절차

In 10 g of ethyl acetate were suspended 2.0 g of 2,4,5-trimethoxybenzoic acid (1a) and 1.45 g of NaBr in a stream of argon, to which 4.0 g of BF3.Et2O was then added dropwise at 25° C., followed by heat stirring at 40° C. for 3 hours. The reaction mixture was cooled with ice, to which 10 mL of water was then added dropwise at 10° C., followed by dropwise adding 7.5 g of a 25% (w/w) sodium hydroxide aqueous solution. Thereto was further added 10 mL of water before stirring, followed by filtering off insoluble inorganic matter. To the separated aqueous layer was dropwise added 3.94 g of 35% hydrochloric acid, followed by stirring for 10 minutes. The precipitated crystal was collected by filtration and washed with water. The resultant crystal was then dried under reduced pressure at 60° C. to provide 1.7 g of 2-hydroxy-4,5-dimethoxybenzoic acid (2a) at a yield of 91%.

후처리

  1. temperatureby heat
  2. additionwas then added dropwise at 10° C.
  3. stirringbefore stirring
  4. filtrationby filtering off insoluble inorganic matter
  5. stirringby stirring for 10 minutes
  6. filtrationThe precipitated crystal was collected by filtration
  7. washwashed with water
  8. customThe resultant crystal was then dried under reduced pressure at 60° C.

출처 및 근거

ORD 기록
ord-a5126c13cb174211811fcc74d1968deb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841461B2

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