Hydrochloric Acid → HCID 86732651、化合物

HRID 523334

反応式

HRID 523334 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86732651HCID 86732651、化合物収率 29.2%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f5c0ee6d1ee425da546ecc9bd12cda8
出典データセット
uspto-grants-2016_05
特許番号
US09334366B2

関連ノート

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