Ethanethiol → Ethyl 2-(4-hydroxyphenoxy)acetate

HRID 2422210Notes

Reaction equation

HRID 2422210 reaction equation
C[O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>ClCCl.C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 240125Ethyl 2-(4-methoxyphenoxy)acetateHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetateYield 75.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl (4-methoxyphenoxy)acetate (2.0 g, 9.5 mmol), ethanethiol (2.8 mL, 38 mmol) and aluminum chloride (5.1 g, 38 mmol) in dichloromethane (20 mL) was stirred under ice-cooling for 40 min. The reaction mixture was poured into a mixture of chloroform and saturated aqueous sodium hydrogencarbonate, and filtered through celite. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-diisopropyl ether to give the title compound (1.4 g, yield 75%).

Workup

  1. temperaturecooling for 40 min
  2. filtrationfiltered through celite
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-a0108817cb234e73862633c9d1a89e45
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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