Methyl bromoacetate → p-Decyloxybenzoyloxy acetic acid methyl ester

HRID 2164333Notes

Reaction equation

HRID 2164333 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4]Br.[CH2:7]([O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Na]>CO>[CH3:1][O:2][C:3](=[O:6])[CH2:4][O:24][C:22](=[O:23])[C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetate2×HCID 1385274-(Decyloxy)benzoic acidHCID 5360545Sodium

Product 1

HCID 54292087p-Decyloxybenzoyloxy acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the addition of 11.2 g (73 mMols) of bromoacetic acid methyl ester, a suspension of 20 g (67 mMols) of p-decyloxybenzoic acid, sodium salt, in 100 ml of methanol was heated for 3 hours and, after the addition of another 2 ml of bromoacetic acid methyl ester, for another 1.5 hours to boiling temperature. After the volatile constituents had been distilled off, the residue was extracted cold with methylene chloride, the solution was washed with water, concentrated by evaporation, the oily residue was taken up in petroleum ether, the solution was treated with active carbon and then reconcentrated by evaporation. p-decyloxybenzoyloxy acetic acid methyl ester melting at 30° to 32° C. was obtained in a yield of 15.8 g (68%). Purification by column chromatography (SiO2, Merck/methylene chloride:toluene=7:3) produced pure ester melting at 32.5° to 34° C.

Workup

  1. distillationAfter the volatile constituents had been distilled off
  2. extractionthe residue was extracted cold with methylene chloride
  3. washthe solution was washed with water
  4. concentrationconcentrated by evaporation
  5. additionthe solution was treated with active carbon
  6. customreconcentrated by evaporation

Sources & evidence

ORD record
ord-359918081dbd426f8e6e1694006e3433
Source dataset
uspto-grants-1985_03
Patent number
US04503244

Reaction notes

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