Ethyl bromoacetate → [4-(4,4,5,5-Tetramethyl-(1,3]dioxolan-2-yl)-phenoxy]-acetic acid ethyl ester

HRID 425930Notes

Reaction equation

HRID 425930 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][CH:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C.C(OCC)(=O)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)[CH3:29]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 44055284-(4,4,5,5-Tetramethyl-1,3-dioxolan-2-yl)phenol

Product 1

HCID 66701800[4-(4,4,5,5-Tetramethyl-(1,3]dioxolan-2-yl)-phenoxy]-acetic acid ethyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-[1,3]dioxolan-2-yl)-phenol (10.0 g, 45.5 mmol) and Cs2CO3 (23.5 g, 68.25 mmol) in DMF (60 mL) was added ethyl α-bromoacetate (11.6 g, 68.25 mmol). The mixture was stirred at room temperature for 24 hours, then diluted with ethyl acetate, washed with water, dried over Na2SO4. After filtration and evaporation, the residue was dried under high vacuum to provide [4-(4,4,5,5-tetramethyl-[1,3]dioxolan-2-yl)-phenoxy]-acetic acid ethyl ester (12.52 g, 90% yield) as an oil.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and evaporation
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-05b6b26d3ff1459f9e3f775a03131bf9
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

Loading…