Diethyl Ether → Methyl alpha-(2,6-diallyl-4-hydroxyphenoxy)4-chlorobenzeneacetate

HRID 1727292Notes

Reaction equation

HRID 1727292 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([O:10]CC2C=CC=CC=2)[CH:7]=[C:6]([CH2:18][CH:19]=[CH2:20])[C:5]=1[OH:21])[CH:2]=[CH2:3].Br[CH:23]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].CCOCC>CN(C=O)C>[CH2:18]([C:6]1[CH:7]=[C:8]([OH:10])[CH:9]=[C:4]([CH2:1][CH:2]=[CH2:3])[C:5]=1[O:21][CH:23]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25])[CH:19]=[CH2:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetateHCID 219859512,6-Diallyl4-benzyloxyphenol

Product 1

HCID 21985939Methyl alpha-(2,6-diallyl-4-hydroxyphenoxy)4-chlorobenzeneacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-diallyl-4-benzyloxyphenol (200 mg, 1.0 eq) in DMF (8 mL) were added methyl α-bromo-4-chlorobenzeneacetate (190 mg, 1.0 eq) and Cs2CO3 (285 mg, 1.2 eq). The reaction mixture was stirred at room temperature for 15 h, poured into ether, washed with water and brine, dried over MgSO4, filtered, and concentrated in vac. Purification by chromatography (SiO2, EtOAc/Hexanes 1:20) afforded the desired methyl α-(2,6-diallyl-4-hydroxyphenoxy)4-chlorobenzeneacetate.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vac
  5. customPurification by chromatography (SiO2, EtOAc/Hexanes 1:20)

Sources & evidence

ORD record
ord-c0ccc17d636044678b4b9f5d896aded0
Source dataset
uspto-grants-2009_02
Patent number
US07495020B2

Reaction notes

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