Water → 2-Dimethylaminoethyl benzoate

HRID 1195421Notes

Reaction equation

HRID 1195421 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-1c6401c7245645ccb052a37d8be74ee4
Source dataset
uspto-grants-1992_05
Patent number
US05110977

Reaction notes

Loading…