4-Fluoro-α-(1-hydroxy-1-methylethyl)benzeneacetic acid → 3-Methyl-2-(p-fluorophenyl)crotonic acid

HRID 1416085노트

반응식

HRID 1416085 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12](O)([CH3:14])[CH3:13])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[C:12]([CH3:14])[CH3:13])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

참가 물질

3

반응물 1

HCID 109548534-Fluoro-α-(1-hydroxy-1-methylethyl)benzeneacetic acid

생성물 1

HCID 110197243-Methyl-2-(p-fluorophenyl)crotonic acid수율 734%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

90 g of polyphosphoric acid were placed in a 350 ml sulphonation flask. Then, it was treated dropwise with a solution of 10.0 g (47 mmol) of 2-(p-fluorophenyl)-3-hydroxy-3-methylbutyric acid in 70 ml of CH2CL2 at 20-25°. The viscous, yellow colored mixture was stirred for 2 hours, with the temperature rising to 35°. After hydrolysis with ice-water the mixture was left to stand overnight and then treated with ether. The organic phase was separated, washed 3 times with water, dried over MgSO4, filtered and the filtrate was concentrated. The residue was dissolved in CH2CL2 and the solution was treated with hexane and concentrated on a rotary evaporator until crystallization occurred. After standing at RT for 1 hour the crystals were filtered off under suction and washed with cold hexane. There were obtained 67 g (73%) of 2-(p-fluorophenyl)-3-methylcrotonic acid as a white powder.

후처리

  1. customrising to 35°
  2. waitwas left
  3. waitto stand overnight
  4. customThe organic phase was separated
  5. washwashed 3 times with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. dissolutionThe residue was dissolved in CH2CL2
  10. additionthe solution was treated with hexane
  11. concentrationconcentrated on a rotary evaporator until crystallization
  12. waitAfter standing at RT for 1 hour
  13. filtrationthe crystals were filtered off under suction
  14. washwashed with cold hexane

출처 및 근거

ORD 기록
ord-00e946fb3a4f487dba43e990ca03c52b
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910606

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