Potassium Carbonate → Methyl 2-(4-phenoxybut-1-yloxy)-phenylacetate

HRID 1085336

Reaction equation

HRID 1085336 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].C(=O)([O-])[O-].[K+].[K+].[O:19]([CH2:26][CH2:27][CH2:28][CH2:29]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.C(OCC)C>[O:19]([CH2:26][CH2:27][CH2:28][CH2:29][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70986(4-Bromobutoxy)benzeneHCID 89719Methyl (2-hydroxyphenyl)acetate

Product 1

HCID 14550847Methyl 2-(4-phenoxybut-1-yloxy)-phenylacetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

28.2 g (0.17 mole) of methyl 2-hydroxyphenylacetate, 25.8 g (0.19 mole) of potassium carbonate and 38.9 g (0.17 mole) of 4-phenoxybutyl bromide in 400 ml of dimethylformamide are stirred for 24 hours at 70° C. Thereafter, the solvent is stripped off and the residue is taken up in diethyl ether. The solution is extracted several times with water and saturated sodium carbonate solution and the organic phase is dried over MgSO4. The oil obtained after removal of the solvent is purified by chromatography over silica gel (cyclohexane/ethyl acetate). Yield: 31 g (58%).

Workup

  1. extractionThe solution is extracted several times with water and saturated sodium carbonate solution
  2. dry with materialthe organic phase is dried over MgSO4
  3. customThe oil obtained
  4. customafter removal of the solvent
  5. customis purified by chromatography over silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-c21204cd35e44371820de599ad217de2
Source dataset
uspto-grants-1991_04
Patent number
US05008438

Linked notes

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