Triethylamine → Acetic acid, [(4-hydroxyphenyl)thio]-, 1,1-dimethylethyl ester

HRID 2253983Notes

Reaction equation

HRID 2253983 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 2401474-Mercaptophenol

Product 1

HCID 10263681Acetic acid, [(4-hydroxyphenyl)thio]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 25.42 g of p-hydroxythiophenol was dissolved in 100 ml of methylene chloride, 20.2 g of triethylamine was dropwise added to the solution under ice cooling. Then, 39.2 g of tert-butyl bromoacetate was added to the mixture followed by reacting at room temperature for an hour. After completion of the reaction, the reaction mixture was washed with 3 times with 1N-HCl and once with saturated sodium chloride aqueous solution. After the organic phase was dried over magnesium sulfate, methylene chloride was distilled off to give tert-butyl (4-hydroxyphenylthio)acetate (quantitative).

Workup

  1. waitby reacting at room temperature for an hour
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed with 3 times with 1N-HCl and once with saturated sodium chloride aqueous solution
  4. dry with materialAfter the organic phase was dried over magnesium sulfate, methylene chloride
  5. distillationwas distilled off

Sources & evidence

ORD record
ord-78765677a61a4195966b5b193bf951ac
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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