Water → ethyl (Z)-3-methyl-4-[4-(1-methylpropoxy)phenoxyl]-2-butenoate

HRID 543339Notes

Reaction equation

HRID 543339 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([CH3:28])=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C)C=O>[CH3:20]/[C:21](/[CH2:28][O:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH:2]([CH3:1])[CH2:3][CH3:4])=[CH:11][CH:10]=1)=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 138820044-(1-Methyl-1-propyloxy)-phenolHCID 53411540Ethyl-4-bromo-3-methyl-but-2-enoate (E/Z; 55/45)

Product 1

HCID 13882007ethyl (Z)-3-methyl-4-[4-(1-methylpropoxy)phenoxyl]-2-butenoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-(1-methylpropoxy)phenol (0.84 g, 5.06 mmol) and potassium carbonate (0.66 g, 0.48 mmol) in 10 ml of dimethylformamide (DMF) at 5° is added ethyl 4-bromo-3-methyl-2-butenoate (1.0 g, 0.48 mmol). The mixture is allowed to warm to RT and is stirred at RT for 20 hours. The reaction mixture is poured into water and extracted with ether. The organic layer is washed with 10% sodium hydroxide to remove any starting phenol, dried and the solvent removed. The product is purified by preparative thin layer chromatography (prep. TLC). The second main band is collected to give ethyl (Z)-3-methyl-4-[4-(1-methylpropoxy)phenoxyl]-2-butenoate, MS m/e 292 (M+).

Workup

  1. extractionextracted with ether
  2. washThe organic layer is washed with 10% sodium hydroxide
  3. customto remove any starting phenol
  4. customdried
  5. customthe solvent removed
  6. customThe product is purified by preparative thin layer chromatography (prep. TLC)
  7. customThe second main band is collected

Sources & evidence

ORD record
ord-d9b61874131343f995d550eec3fd420a
Source dataset
uspto-grants-1987_04
Patent number
US04661617

Reaction notes

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