Water → 2-Dimethylaminoethyl benzoate

HRID 1613689Notes

Reaction equation

HRID 1613689 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13][OH:14].[OH-].[Na+].O>C(Cl)Cl>[C:1]([O:14][CH2:13][CH2:12][N:11]([CH3:15])[CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 79022-(Dimethylamino)ethanolHCID 14798Sodium Hydroxide

Product 1

HCID 751582-Dimethylaminoethyl benzoateYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 70.29 g (0.50 mol) of benzoyl chloride in 500 ml of methylene chloride was added to a solution of 44.57 g (0.50 mol) of 2-dimethylaminoethanol, 20.0 g (0.50 mol) of sodium hydroxide and 500 ml of water over 15 minutes with rapid stirring. Stirring was continued for 3.25 hours after which the organic layer was separated, washed with water, dried over MgSO4 and concentrated. Distillation of the residue gave 59.5 g of product; bp=102°-8° C./0.50 mm.

Workup

  1. customafter which the organic layer was separated
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-70af6653888d4f598a1a766d298359df
Source dataset
uspto-grants-1993_03
Patent number
US05194472

Reaction notes

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