Reaction #2329033

ord-2925218ec841453996aaa0e5f0912668

Reaction equation

ClCCl
CH2Cl2
COC(=O)c1ccc(O)cc1
methyl-4-hydroxybenzoate
O=C([O-])[O-].[K+].[K+]
K2CO3
CCCCCCCCCCCCBr
bromododecane
→
CCCCCCCCCCCCOc1ccc(C(=O)OC)cc1
title compound
Yield 95.0%
CCCCCCCCCCCCOc1ccc(C(=O)OC)cc1
Methyl 4-dodecyloxybenzoate
Yield 95.0%

Reactants

ClCCl
CH2Cl2
COC(=O)c1ccc(O)cc1
methyl-4-hydroxybenzoate
O=C([O-])[O-].[K+].[K+]
K2CO3
CCCCCCCCCCCCBr
bromododecane

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherReaction
  2. 2
    Temperaturewas cooled to room temperature
  3. 3
    Otherprecipitated into cold water
  4. 4
    FiltrationThe precipitate was collected by suction filtration
  5. 5
    Otherpurified by re-crystallization from acetone

Procedure

To a thoroughly degassed suspension of K2CO3 (127 g, 921 mmol) in DMF (600 mL) was added methyl-4-hydroxybenzoate (70 g, 461 mmol) and the mixture heated to 70° C. after which was added bromododecane (126 g, 507 mmol) and the reaction allowed to stir at 70° C. under argon for 3 hours, after which TLC (CH2Cl2) showed completion. Reaction was cooled to room temperature and precipitated into cold water. The precipitate was collected by suction filtration and purified by re-crystallization from acetone to give the title compound (140 g, 95%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07671033B2uspto-grants-2010_03