Water → Methyl 3-(4-phthalimidobutoxy)benzoate

HRID 1594434Notes

Reaction equation

HRID 1594434 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33].O>C(#N)C>[C:24]1(=[O:33])[N:23]([CH2:22][CH2:21][CH2:20][CH2:19][O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]12

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 88068Methyl 3-HydroxybenzoateHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 58678553Methyl 3-(4-phthalimidobutoxy)benzoateYield 94.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3-hydroxybenzoate (3.0 g, 19.7 mmol) was dissolved in 50 mL of acetonitrile and K2CO3 (3.27 g, 23.7 mmol) was added. The resulting mixture was reacted with N-(4-bromobutyl)phthalimide (6.68 g, 23.7 mmol) and KI (3.93 g, 23.7 mmol) and stirred overnight at 70° C. Following the addition of water, the resulting mixture was extracted with chloroform. The organic layer was washed with brine. The organic layer was dried with sodium sulfate and then concentrated under reduced pressure, followed by recrystallization with n-hexane/ethyl acetate to give a white crystal (6.60 g, 94.8%).

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customfollowed by recrystallization with n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-990e84470de34c049ff2ecedc9faced3
Source dataset
uspto-grants-2007_11
Patent number
US07301033B2

Reaction notes

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