Sodium Hydroxide → t-Butyl 2-(2-phenylthioethoxy)acetate

HRID 613759Notes

Reaction equation

HRID 613759 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O:15][C:16](=[O:19])[CH2:17]Br)([CH3:14])([CH3:13])[CH3:12].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:1]1([S:7][CH2:8][CH2:9][O:10][CH2:17][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 696852-(Phenylthio)ethanolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 18779057t-Butyl 2-(2-phenylthioethoxy)acetate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-Phenylthioethanol (6.1 g), t-butylbromoacetate (7.9 ml), tetrabutylammoniumbromide (1.3 g), toluene (80 ml), and 75% aqueous sodium hydroxide (40 ml) were stirred together for 72 hours. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organics were washed with brine, dried (MgSO4) and the solvent was removed in vacuo to provide the subtitle compound (12.07 g).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-17adbc8079c74edd863b37a5ccbdf975
Source dataset
uspto-grants-1999_12
Patent number
US06008365

Reaction notes

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