2-Chloroethanol → 2-tert-Butyl-4-(2-hydroxyethoxy)phenol

HRID 1885907Notes

Reaction equation

HRID 1885907 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH2:15](Cl)[CH2:16][OH:17].S(=O)(=O)(O)O>O.[I-].[K+]>[C:1]([C:5]1[CH:11]=[C:10]([O:12][CH2:15][CH2:16][OH:17])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 16043Tert-Butylhydroquinone

Product 1

HCID 183535672-tert-Butyl-4-(2-hydroxyethoxy)phenolYield 47.6%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

332 g (2 mol) of t-butylhydroquinone and 1 g of potassium iodide were dissolved in 2 l of water under nitrogen atmosphere, and were heated to 80° C. Thereafter, to the solution thus obtained, were dropwise added 232 g (2.8 mol) of 48% sodium hydroxide aqueous solution and 200 g (2.5 mol) of ethylene chlorohydrine at the same time for 3 hours while constantly maintaining alkaline. After finishing this dropwise addition, the resultant reaction mixture was heated for 8 hours at the reflux temperature. After cooling the reaction mixture thus obtained, the reaction mixture was neutralized with sulfuric acid and was extracted with toluene. After removing solvent, the remaining material was distilled under reduced pressure and the distillate was recrystallized from toluene to obtain 200 g of 2-t-butyl-4-(2'-hydroxyethoxy)phenol. The reaction formula (alkylation) is illustrated in the following. ##STR4##

Workup

  1. customThereafter, to the solution thus obtained
  2. customfor 3 hours
  3. temperaturewhile constantly maintaining alkaline
  4. additionthis dropwise addition
  5. customthe resultant reaction mixture
  6. temperaturewas heated for 8 hours at the reflux temperature
  7. temperatureAfter cooling the reaction mixture
  8. customthus obtained
  9. extractionwas extracted with toluene
  10. customAfter removing solvent
  11. distillationthe remaining material was distilled under reduced pressure
  12. customthe distillate was recrystallized from toluene

Sources & evidence

ORD record
ord-f0fcf766ae6b4a88877865bba3043c1b
Source dataset
uspto-grants-1992_09
Patent number
US05147902

Reaction notes

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