1-Bromodecane → 4-(Decyloxy)-3-(1,1-dimethylethyl)benzoic acid methyl ester

HRID 1728892Notes

Reaction equation

HRID 1728892 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CC(=O)CC>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:6]([C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=1

Participants

6

Reactant 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoate

Product 1

HCID 539263074-(Decyloxy)-3-(1,1-dimethylethyl)benzoic acid methyl esterYield 105.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 12.0 g of 3-(1,1-dimethylethyl)-4-hydroxybenzoic acid methyl ester, 11.15 g of 1-bromodecane, 9.95 g of potassium carbonate, 0.797 g of potassium iodide and 100 ml of 2-butanone is heated at reflux temperature for 40 hours. The reaction is cooled, filtered and the filtrate concentrated in vacuo. The residue is purified by chromatography (silica gel: 0-3% ethyl acetate/hexane) to give 18.49 g of the desired product as a light yellow oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 40 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue is purified by chromatography (silica gel: 0-3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7f11c824057a4b6ea25ba39b9a052d29
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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