Potassium Carbonate → Ethyl 2-(m-tert-butyl-p-hydroxyphenoxy)tetradecanoate

HRID 1112077Notes

Reaction equation

HRID 1112077 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].Br[CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:7][C:6]1[CH:8]=[CH:9][C:10]([O:12][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16043Tert-ButylhydroquinoneHCID 85791Tetradecanoic acid, 2-bromo-, ethyl ester

Product 1

HCID 3015607Ethyl 2-(m-tert-butyl-p-hydroxyphenoxy)tetradecanoateYield 37.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

116 g of tert-butylhydroquinone, 234 g of ethyl α-bromotetradecanoate and 170 g of potassium carbonate were mixed in 1.6 liters of acetone and reacted for 48 hours under refluxing and stirring. After the reaction, the acetone was distilled off and the residue was dissolved in one liter of ethyl acetate. The organic solvent layer was washed with water, dried with sodium sulfate and concentrated. The residue was recrystallized from 250 ml of n-hexane to obtain 110 g of a white solid. The melting point was 45° to 48° C.

Workup

  1. customreacted for 48 hours
  2. temperatureunder refluxing
  3. customAfter the reaction
  4. distillationthe acetone was distilled off
  5. dissolutionthe residue was dissolved in one liter of ethyl acetate
  6. washThe organic solvent layer was washed with water
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was recrystallized from 250 ml of n-hexane

Sources & evidence

ORD record
ord-4c7b4f0e75604a328e7a60bee4c2460d
Source dataset
uspto-grants-1978_10
Patent number
US04120723

Reaction notes

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