Hydrochloric Acid → HCID 86732651, compound

HRID 523334

Reaction equation

HRID 523334 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 86732651HCID 86732651, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9f5c0ee6d1ee425da546ecc9bd12cda8
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Linked notes

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