Hydroquinone → Ethyl N-[2-(4-hydroxyphenoxy)ethyl]carbamate

HRID 2309835Notes

Reaction equation

HRID 2309835 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Cl[CH2:10][CH2:11][NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].CCCCCC>CN(C)C=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:10][CH2:11][NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 8058Hexane2×HCID 11430Potassium CarbonateHCID 80621Ethyl 2-chloroethylcarbamate

Product 1

HCID 14552586Ethyl N-[2-(4-hydroxyphenoxy)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of hydroquinone (11.0 g, 100.0 mmol), ethyl 2-chloroethylcarbamate (7.6 g, 50.0 mmol) and potassium carbonate (13.8 g, 100.0 mmol) in 100 ml of dimethylformamide (DMF) is heated at 80° for 20 hours. After cooling to RT, the reaction mixture is poured into ice water and hexane, and the hexane layer is discarded to remove the bis ether by-product. The aqueous layer is then extracted with ether (3X) and the combined ether layers are washed with water, followed with brine, and dried over calcium sulfate. The solvent is removed and the residue is diluted with chloroform to precipitate out the excess hydroquinone. Following filtration, the filtrate is collected and rotoevaporated to give ethyl N-[2-(4-hydroxyphenoxy)ethyl]carbamate, a solid.

Workup

  1. temperatureis heated at 80° for 20 hours
  2. customto remove the bis ether by-product
  3. extractionThe aqueous layer is then extracted with ether (3X)
  4. washthe combined ether layers are washed with water
  5. dry with materialdried over calcium sulfate
  6. customThe solvent is removed
  7. additionthe residue is diluted with chloroform
  8. customto precipitate out the excess hydroquinone
  9. filtrationfiltration
  10. customthe filtrate is collected

Sources & evidence

ORD record
ord-7752129b371945e08c655ccbfa70afe2
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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