Water → HCID 15783311, compound

HRID 987839Notes

Reaction equation

HRID 987839 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21].O>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([O:6][CH2:21][CH:20]=[CH2:19])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 101942,4,6-Trimethylbenzoic acidHCID 11430Potassium Carbonate

Product 1

HCID 15783311HCID 15783311, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,6-trimethylbenzoic acid (10 g, 61 mmol) in DMF (100 mL) were sequentially added potassium carbonate (17 g, 122 mmol) and allyl bromide (11 g, 91.5 mmol). The mixture was stirred at rt overnight before it was poured into water (˜1 L). The resulted precipitate was filtered and washed with water, then dried in vacuo to give allyl 2,4,6-trimethylbenzoate as a solid (10.2 g, 82%) which was nitrated and then reduced as shown for Example 14 (procedure B and C) to give allyl 3-amino-2,4,6-trimethylbenzoate.

Workup

  1. filtrationThe resulted precipitate was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1cca2f0fcd1b443798b810e37e23f354
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

Loading…