Ethyl bromoacetate → HCID 21986425, compound

HRID 9630Notes

Reaction equation

HRID 9630 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([OH:10])=[C:5]([CH3:11])[CH:4]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:10][C:6]1[C:5]([CH3:11])=[CH:4][C:3]([CH2:2][OH:1])=[CH:8][C:7]=1[CH3:9])[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 2786604-(hydroxymethyl)-2,6-dimethylphenol

Product 1

HCID 21986425HCID 21986425, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(hydroxymethyl)-2,6-dimethylphenol (P. Claus et al., Monatsh. Chem. 1972, 103(4), 1178–1193) (1.9 g) in acetonitrile (50 ml) was treated with ethyl bromoacetate (2.17 g) and caesium carbonate (4.24 g) and the mixture stirred at room temperature overnight. The solution was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was collected, dried over magnesium sulfate and filtered. The filtrate was concentrated to give the title compound as a yellow oil.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was collected
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-42f38fc69f714700a45eeb1a3594703c
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Reaction notes

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