Hydrochloric Acid → HCID 86732651, 화합물

HRID 523334

반응식

HRID 523334 반응식
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Br[CH2:15][CH2:16][CH2:17][OH:18].C([O-])([O-])=O.[K+].[K+].Cl>CN1C(=O)CCC1>[OH:18][CH2:17][CH2:16][CH2:15][O:12][C:9]1[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:13])=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 92203Methyl p-coumarate

생성물 1

HCID 86732651HCID 86732651, 화합물수율 29.2%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

15 g (84.2 mmol) of 4-hydroxycinnamic acid methyl ester, 14 g (101 mmol) of 3-bromo-1-propanol, 23.4 g of K2CO3 are dissolved in 90 mL of NMP. The solution is heated up to 80° C. and stirred for 20 hours. Then, the reaction mixture is cooled down to room temperature and carefully acidified with 1N HCl solution. The solution is extracted with ethylacetate. The organic phase is dried over sodium sulfate, filtrated and concentrated under reduced pressure. Chromatography of the residue on silica gel using hexane:ethyl acetate 7:3 as eluent yielded 5.8 g of methyl (2E)-3-[4-(3-hydroxypropoxy)phenyl]prop-2-enoate as a white solid.

후처리

  1. temperatureThen, the reaction mixture is cooled down to room temperature
  2. extractionThe solution is extracted with ethylacetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9f5c0ee6d1ee425da546ecc9bd12cda8
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334366B2

연결된 노트

불러오는 중…