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

HRID 247940Notes

Reaction equation

HRID 247940 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 gel: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 gel:0-3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e3513c6bccae404996e68d578b4d6394
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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