Acetic Acid → HCID 53706497, compound

HRID 851521Notes

Reaction equation

HRID 851521 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([OH:12])=[CH:4][C:3]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15].[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]C.C[O-].[Na+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:9])[CH3:10])[C:5]([OH:12])=[CH:4][C:3]=1[CH2:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9571-OctanolHCID 10942334Sodium Methoxide2×HCID 20501412HCID 20501412, compound

Product 1

HCID 53706497HCID 53706497, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 200-ml four-necked flask, were charged 23.6 g of methyl (2-methyl-4-t-butyl-5-hydroxyphenyl)acetate, 13.0 g of octylalcohol and 0.5 g of sodium methoxide. The mixture was allowed to react at 120° C. for 2 hours, and then at 140° to 150° C. under a reduced pressure of 20 mmHg for 5 hours. During the course of this reaction, along with the progress of reaction 1.5 g of sodium methoxide was added in three equal portions. After completion of the reaction, the reaction mixture was cooled to 80° C., neutralized with glacial acetic acid, then dissolved in toluene, washed with water, dried over anhydrons sodium sulfate, and freed from the solvent under reduced pressure to obtain 29.4 g (88% yield) of viscous octyl 2-methyl-4-t-butyl-5-hydroxyphenylacetate.

Workup

  1. customto react at 120° C. for 2 hours
  2. customDuring the course of this reaction
  3. additionwas added in three equal portions
  4. customAfter completion of the reaction
  5. washwashed with water
  6. dry with materialdried over anhydrons sodium sulfate

Sources & evidence

ORD record
ord-8b86b6f6325d43eb883536643d57e429
Source dataset
uspto-grants-1983_05
Patent number
US04385143

Reaction notes

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