Thionyl Chloride → HCID 53756718, compound

HRID 619551Notes

Reaction equation

HRID 619551 reaction equation
[C:1]([C:5]1[C:6]([OH:20])=[C:7]([CH2:15][CH2:16][C:17](O)=[O:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[C:6]([OH:20])=[C:7]([CH2:15][CH2:16][C:17]([Cl:23])=[O:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19429801HCID 19429801, compound

Product 1

HCID 53756718HCID 53756718, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Operating under a nitrogen current, 29.8 g of methyl 3-(3',5'-di-tert-butylhydroxyphenyl)propionate, 80 mL of ethanol, and 6 g of sodium hydroxide were introduced in a 0.5-L four-neck flask equipped with a stirrer, addition funnel, and thermometer and were stirred for 1 hour while heating under reflux. After completion of the stirring period, the ethanol was removed by distillation and the reaction mass was then neutralized by the gradual addition of concentrated hydrochloric acid. 150 mL of a 1:1 liquid mixture of toluene and ethyl acetate was added followed by washing twice with water. The solvent was subsequently distilled from the washed organic layer to give 27.2 g of 3-(3',5'-di-text-butylhydroxyphenyl)propionic acid in crystalline form. Then, while operating under a nitrogen current, 8.0 g of this 3-(3',5'-di-tert-butylhydroxyphenyl)propionic acid and 50 mL of dry toluene were introduced into a 0.2-L four-neck flask equipped with a stirrer, addition funnel, and thermometer and were stirred. After completion of stirring, 4 g of thionyl chloride was added dropwise at room temperature from the addition funnel. The reaction solution was then heated to 70° C. and a reaction was run for 4 hours with stirring. After completion of the reaction, the by-products were distilled under reduced pressure from the reaction solution to give 8.1 g of 3-(3',5'-di-tert-butylhydroxyphenyl)propionyl chloride in crystalline form.

Workup

  1. customequipped with a stirrer, addition funnel
  2. stirringAfter completion of stirring
  3. stirringwith stirring
  4. customAfter completion of the reaction
  5. distillationthe by-products were distilled under reduced pressure from the reaction solution

Sources & evidence

ORD record
ord-34435c5ebbe241858009d158a3e3e646
Source dataset
uspto-grants-1999_09
Patent number
US05959057

Reaction notes

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