2-Chloroethanol → HCID 52527969, compound

HRID 1799223Notes

Reaction equation

HRID 1799223 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[H-].[Na+].Cl[CH2:16][CH2:17][OH:18]>CC(N(C)C)=O>[OH:18][CH2:17][CH2:16][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([N:2]([CH3:12])[CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 120924-(Dimethylamino)benzoic acidHCID 24758Sodium hydride

Product 1

HCID 52527969HCID 52527969, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Conditions

Temperature
105 °C

Procedure

17.5 g (0.106 mol) of 4-dimethylamino benzoic acid was dissolved in 80 mL of dimethyl acetamide and added drop wise over 30 minutes to a suspension of 5.32 g (0.133 mol) of sodium hydride (60% in mineral oil) in 50 mL dimethyl acetamide. It became difficult to stir the suspension and an additional 30 mL of dimethyl acetamide was added. 7.2 mL (8.64 g, 0.107 mol) of 2-chloro-ethanol was added and the reaction mixture was heated to 105° C. The reaction was allowed to continue 16 hours at 105° C. The mixture was allowed to cool down to room temperature and the formed sodium chloride was removed by filtration. The solvent was removed under reduced pressure and the residue was crystallized from 400 mL of methanol/water 1/7. The crude 2-hydroxyethyl-(4-dimethylamino benzoate) was isolated by filtration and recrystallized from 200 mL of methanol/water 1/3. 15 g of 2-hydroxyethyl-(4-dimethylamino benzoate) was isolated (m.p. 88-90°).

Workup

  1. additionadded drop wise over 30 minutes
  2. temperatureto cool down to room temperature
  3. customthe formed sodium chloride was removed by filtration
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was crystallized from 400 mL of methanol/water 1/7

Sources & evidence

ORD record
ord-36952f1ff5b646cabb2650ad189c1eeb
Source dataset
uspto-grants-2013_01
Patent number
US08344038B2

Reaction notes

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