Methylparaben → Methyl 4-(2-bromoethoxy)benzoate

HRID 1264085Notes

Reaction equation

HRID 1264085 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]Br.C(=O)([O-])[O-].[K+].[K+]>>[Br:12][CH2:13][CH2:14][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

4

Reactant 3

HCID 7456MethylparabenHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 1898264Methyl 4-(2-bromoethoxy)benzoateYield 99%

Procedure

Methyl 4-hydroxybenzoate (5.0 g, 32.86 mmol) was combined with 1,2-dibromoethane (35 mL) and potassium carbonate (6.8 g, 49.23 mmol, 1.5 eq.) then heated at reflux for 18 h. The reaction mixture was concentrated under reduced pressure then the residue partitioned between ethyl ether (500 mL) and water (200 mL). The ether was extracted with 2 N sodium hydroxide (5×50 mL). The solvent was removed under reduced pressure to give the desired product as a white solid (8.47 g, 99%).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 18 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue partitioned between ethyl ether (500 mL) and water (200 mL)
  5. extractionThe ether was extracted with 2 N sodium hydroxide (5×50 mL)
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ca26c2179cc1471c8ab3e71b7c226942
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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