Ethanol → Ethyl 2-(2,4-di-tert-butylphenoxy)caproate

HRID 362692Notes

Reaction equation

HRID 362692 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].Br[CH:20]([CH2:26][CH2:27][CH2:28][CH3:29])[C:21]([O:23][CH2:24][CH3:25])=[O:22].CCO>CO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][CH:20]([CH2:26][CH2:27][CH2:28][CH3:29])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 73112,4-Di-tert-butylphenolHCID 79072Ethyl 2-bromohexanoateHCID 10942334Sodium Methoxide

Product 1

HCID 11100155Ethyl 2-(2,4-di-tert-butylphenoxy)caproateYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
140 °C

Procedure

206 g (1 mol) of 2,4-di-tert-butylphenol were melted and heated to 140° C. under nitrogen. 185 g (1.03 mol) of a 30% strength NaOMe solution in MeOH and 245 g (1.1 mol) of ethyl 2-bromocaproate were metered in simultaneously in the course of 1 hour. During the addition, a mixture of MeOH and EtOH was distilled off. After the addition, the reaction to give the ester mixture was complete. The mixture was cooled to 80° C., 20 g of NaOMe solution were added and 750 ml of ethanol were then added in the course of 4 hours. A methanol/ethanol mixture distilled off at an overhead temperature of initially 74° to 76° C. At the end, the temperature was increased to 90° C. and pure ethanol distilled over at 78° to 79° C. For isolation, 250 ml of water were added. After separation of the phases and renewed washing with 200 ml of water, 351 g of a viscous yellow oil of the following composition (0.3% of ethyl bromocaproate, 0.7 g of residual phenol, 98% of ethyl 2-(2,4-di-tert-butylphenoxy)caproate and 0.3% of methyl 2-(2,4-ditert-butylphenoxy)caproate, remained. This corresponds to a yield of 98.8% of theory, based on the phenol employed.

Workup

  1. customsimultaneously in the course of 1 hour
  2. additionDuring the addition
  3. distillationwas distilled off
  4. additionAfter the addition
  5. customthe reaction

Sources & evidence

ORD record
ord-0ee89acdd81c43b685328bf04f38e85d
Source dataset
uspto-grants-1999_02
Patent number
US05869735

Reaction notes

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