1-Bromopentane → Dimethyl 4-pentyloxyphthalate

HRID 850491Notes

Reaction equation

HRID 850491 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>CN(C=O)C>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 89726Dimethyl 4-hydroxyphthalate

Product 1

HCID 19363307Dimethyl 4-pentyloxyphthalateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Dimethyl 4-hydroxyphthalate (10.0 g, 47 mmol) was dissolved in DMF (100 ml), and potassium carbonate (30 g, 217 mmol) and n-amyl bromide (10 ml, 80 mmol) were added to this solution. The mixture was stirred at 90° C. for 2 hours, and the solid was removed by filtration through Celite. The filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1) to give dimethyl 4-pentyloxyphthalate (12.7 g, 45.4 mmol, 97%) as a colorless oil.

Workup

  1. customthe solid was removed by filtration through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-55532753ea0b4328abea3017e68adcbc
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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