Water → n-Octadecyl 4-tert.-butyl-2,6-dimethyl-3-hydroxyphenylacetate

HRID 1448770Notes

Reaction equation

HRID 1448770 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]([OH:15])=[O:14])=[C:7]([CH3:16])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2].[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]([O:15][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])=[O:14])=[C:7]([CH3:16])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8221Stearyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 203459052-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid

Product 1

HCID 20345920n-Octadecyl 4-tert.-butyl-2,6-dimethyl-3-hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.68 grams of the compound of Example 5, 11.4 grams of n-octadecanol and 0.8 grams of p-toluene sulfonic acid monohydrate were dispersed in 150 ml of toluene and heated at reflux for seven hours during which the water collected by azeotropic distillation was almost equal to the theory. The reaction mixture was successively washed with water, aqueous saturated sodium bicarbonate solution, and then with water once again until the wash water was neutral. After drying over anhydrous sodium sulfate and filtering free of the drying agent, the clear filtrate was evaporated at reduced pressures to yield the desired product as residue. After successive crystallizations from acetonitrile and n-heptane, the desired compound was isolated as white crystals melting at 57° to 59° C. (Compound 1).

Workup

  1. temperatureheated
  2. distillationcollected by azeotropic distillation
  3. washThe reaction mixture was successively washed with water, aqueous saturated sodium bicarbonate solution
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. filtrationfiltering free of the drying agent
  6. customthe clear filtrate was evaporated at reduced pressures

Sources & evidence

ORD record
ord-3874937b3a9540b1851a8cd002efc18f
Source dataset
uspto-grants-1980_02
Patent number
US04187246

Reaction notes

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