Methyl 4-(decyloxy)benzoate → HCID 53678394, compound

HRID 2164332Notes

Reaction equation

HRID 2164332 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1.[CH3:22][O-:23].[Na+]>COCCOCCO>[CH3:22][O:23][CH2:4][CH2:3][O:2][CH2:1][CH2:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3574987Methyl 4-(decyloxy)benzoateHCID 10942334Sodium Methoxide

Product 1

HCID 53678394HCID 53678394, compound

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

A mixture of 25 g (0.09 mol) of p-decyloxybenzoic acid methyl ester and 100 ml of diethylene glycol monomethyl ether was heated for 6 hours to 150° C. with a spatula tip of sodium methanolate. After the excess diethylene glycol monomethyl ether had been distilled off, the residue was taken up in methylene chloride, the solution was washed with water, treated with active carbon and concentrated by evaporation. 24.5 g (72%) of slightly contaminated p-decyloxybenzoic acid 2-(2-methoxyethoxy)-ethyl ester were obtained. Purification by column chromatography (SiO2, Merck/methylene chloride+5% of methanol) produced pure ester having a refractive index nD20 of 1.4945.

Workup

  1. distillationAfter the excess diethylene glycol monomethyl ether had been distilled off
  2. washthe solution was washed with water
  3. additiontreated with active carbon
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7aa5a88ca498406ca2f514df28d3a323
Source dataset
uspto-grants-1985_03
Patent number
US04503244

Reaction notes

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