Methylparaben → Methyl 4-(3-bromopropoxy)benzoate

HRID 2108364Notes

Reaction equation

HRID 2108364 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Br:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 3709742Methyl 4-(3-bromopropoxy)benzoateYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-hydroxybenzoate (1.52 g, 10 mmol), 1,3-dibromo-propane (20.3 mL, 200 mmol) and potassium carbonate (4.2 g, 30 mmol) in 100 mL of dry CH3CN was heated at 70° C. for 5.0 hr. After cooling to room temperature, the reaction mixture was filtered through a pad of Celite and rinsed with CH3CN. The combined filtrates were concentrated in vacuo and purified by ISCO (Hexane-ethyl acetate: 80:20 to 0:100) on silica gel to afford 107A (2.44 g, 89%) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through a pad of Celite
  3. washrinsed with CH3CN
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. custompurified by ISCO (Hexane-ethyl acetate: 80:20 to 0:100) on silica gel

Sources & evidence

ORD record
ord-dbb15955d56d48f7a397e8e809761c85
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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