Dichloromethane → 2-Dimethylaminoethyl benzoate

HRID 2081931Notes

Reaction equation

HRID 2081931 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][OH:17].[Na]>O>[C:1]([O:17][CH2:16][CH2:15][N:14]([CH3:18])[CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 79022-(Dimethylamino)ethanolHCID 5360545Sodium

Product 1

HCID 751582-Dimethylaminoethyl benzoateYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 70.29 grams (0.50 mol) of benzoyl chloride in 500 milliters of methylene chloride was added to a solution of 44.57 grams (0.50 mol) of 2-dimethylaminoethanol, 20.0 grams (0.50 mol) of sodium hydroxideand 500 milliters 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 grams of product; bp=102°-108° C./0.50 min.

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-465c8eaff8b445fea94bfd691e61a542
Source dataset
uspto-grants-1993_02
Patent number
US05187037

Reaction notes

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