Dimethylformamide → Methyl 4-(3-chloropropoxy)-alpha-methylcinnamate

HRID 359073Notes

Reaction equation

HRID 359073 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[C:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][Cl:30]>O>[Cl:30][CH2:29][CH2:28][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 53733305Methyl 4-hydroxy-alpha-methylcinnamate

Product 1

HCID 53772867Methyl 4-(3-chloropropoxy)-alpha-methylcinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-hydroxy-α-methylcinnamate (16.3 g), DMF (50 ml) and anhydrous potassium carbonate (11.7 g) were mixed, and stirred at 90° C. for 1 hour. The reaction solution was allowed to cool to 50° C., added 1-bromo-3-chloropropane (8.4 ml) thereto, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added water (200 ml), and the mixture was extracted with ether (150 ml), washed with water (150 ml) 2 times, and then, dried over anhydrous magnesium sulfate. The ether layer was concentrated urder reduced pressure to give methyl 4-(3-chloropropoxy)-α-methylcinnamate (20 g).

Workup

  1. temperatureto cool to 50° C.
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. extractionthe mixture was extracted with ether (150 ml)
  4. washwashed with water (150 ml) 2 times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe ether layer was concentrated urder reduced pressure

Sources & evidence

ORD record
ord-79b2f366874b4317b070302be60b5fc8
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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