Myristyl bromide → 3-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoic acid methyl ester

HRID 1728815Notes

Reaction equation

HRID 1728815 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][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])=[C:6]([C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=1

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoate

Product 1

HCID 538584113-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 30.0 g 3-(1,1-dimethylethyl)-4-hydroxybenzoic acid methyl ester, 42.9 ml of 1-bromotetradecane, 47.8 g of potassium carbonate and 700 ml of acetone is refluxed for 48 hours. The cooled reaction is filtered, concentrated in vacuo and purified by column chromatography (silica ge1:0-3% ethyl acetate/hexane) to give 38.8 g of the desired product as colorless prisms.

Workup

  1. temperatureis refluxed for 48 hours
  2. customThe cooled reaction
  3. filtrationis filtered
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (silica ge1:0-3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-09c2ee71089d42ebad72648df48969d2
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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