2-Chloroethanol → HCID 20716711, compound

HRID 2308126Notes

Reaction equation

HRID 2308126 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.C([O-])([O-])=O.[K+].[K+].Cl[CH2:21][CH2:22][OH:23]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:21][CH2:22][OH:23])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 92203Methyl p-coumarate

Product 1

HCID 20716711HCID 20716711, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 g (168 mmol) of 3-(4-hydroxyphenyl)acrylic acid methyl ester, 29 g (210 mmol) of anhydrous K2CO3 and a spatula tip of KI were placed in 200 ml of dimethylformamide. 14.91 g (185 mmol) of 2-chloroethanol were added dropwise at 85° C. within 5 minutes while stirring. The batch was stirred at 85° C. for a further 3 days. Subsequently, the salts were filtered off and the filtrate was concentrated to dryness in a water-jet vacuum. 16.1 g of (E)-3-[4-[2-hydroxyethoxy]phenyl]acrylic acid methyl ester were obtained in the form of white crystals after recrystallization from i-propanol.

Workup

  1. stirringThe batch was stirred at 85° C. for a further 3 days
  2. filtrationSubsequently, the salts were filtered off
  3. concentrationthe filtrate was concentrated to dryness in a water-jet vacuum

Sources & evidence

ORD record
ord-50c54d14fd8e470b9de1cd1225b8e8ce
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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