Hydrochloric Acid → Ethyl (3,5-di-t-butyl-4-hydroxyphenyl)-acetate

HRID 850332Notes

Reaction equation

HRID 850332 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]([OH:19])=[O:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:21](O)[CH3:22]>>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]([O:19][CH2:21][CH3:22])=[O:18])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27751103,5-Bis(1,1-dimethylethyl)-4-hydroxybenzeneacetic acid

Product 1

HCID 13908126Ethyl (3,5-di-t-butyl-4-hydroxyphenyl)-acetateYield 90%

Procedure

In ethanol (60 mL) was dissolved 3,5-di-t-butyl-4-hydroxyphenyl-acetic acid (8.0 g, 30.3 mmol). The solution was saturated with HCl gas and stirred at room temperature for 18 hours. The mixture was evaporated in vacuo and the residue was dissolved in ethyl acetate (100 mL). The organic phase was washed with water (100 mL) and then brine (100 mL). The organic phase was dried over magnesium sulfate and evaporated in vacuo to give 7.95 g (90%) of the product as an oil.

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washThe organic phase was washed with water (100 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-eb9e8c6ce080490dbbdccf1bde12e274
Source dataset
uspto-grants-2000_01
Patent number
US06017918

Reaction notes

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