Tris(hydroxymethyl)aminomethane → Methyl 2-{[4-(2-hydroxyethyl)phenoxy]methyl}benzoate

HRID 2112001Notes

Reaction equation

HRID 2112001 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+].C(O)C(N)(CO)CO>C(#N)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 10393TyrosolHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 58820416Methyl 2-{[4-(2-hydroxyethyl)phenoxy]methyl}benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2-Hydroxyethyl)phenol (2 g, 14.48 mmol) and methyl 2-(bromomethyl)benzoate (3.48 g, 15.20 mmol) was dissolved in acetonitrile (20 ml). Potassium carbonate anhydrous (4.0 g, 28.95 mmol) was added. After stirring at 60° C. for three hours PS-trisamine was added (0.2 eq) and was stirred overnight. The PS-trisamine was filtered of and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic layer was washed with 3 portions of water (3×10 ml). The organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 3.732 g of methyl 2-{[4-(2-hydroxyethyl)phenoxy]methyl}benzoate (yield 90%).

Workup

  1. additionwas added (0.2 eq)
  2. filtrationThe PS-trisamine was filtered of and the acetonitrile
  3. customwas removed by evaporation
  4. additionEtOAc (10 ml) was added
  5. washthe organic layer was washed with 3 portions of water (3×10 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-6e35d572e22d46f3aa15442b66614579
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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