Ethylene Glycol → Dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amine

HRID 1468518Notes

Reaction equation

HRID 1468518 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1[C:16]([CH3:17])=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26](O)[CH2:27][OH:28].C1(C)C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:19]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[C:11]([CH3:18])[C:12]([CH:13]2[O:28][CH2:27][CH2:26][O:14]2)=[CH:15][C:16]=1[CH3:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 574610744-Dibenzylamino-2,5-dimethylbenzaldehyde

Product 1

HCID 57461075Dibenzyl-(4-[1,3]dioxolan-2-yl-2,5-dimethyl-phenyl)amineYield 78.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-dibenzylamino-2,5-dimethylbenzaldehyde (3.60 g, 10.9 mmol) in toluene (35.0 mL) under nitrogen was added 1,2-ethanediol (1.83 mL, 32.8 mmol) and p-toluenesulfonic acid (451 mg, 2.62 mmol). The reaction mixture was heated at 80° C. overnight. TLC (3:1 hexanes:EtOAc) showed a ˜50:50 mixture of product and starting material. Magnesium sulfate (1.32 g, 10.9 mmol) was added and stirring was continued for 6 h. The reaction mixture was then filtered and concentrated under reduced pressure to give title compound (3.19 g, 78% yield) as an oil.

Workup

  1. additiona ˜50:50 mixture of product
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df982c16b3044bf1a2277d40d0ca974c
Source dataset
uspto-grants-2015_04
Patent number
US09000173B2

Reaction notes

Loading…