Water → HCID 12423646, compound

HRID 1170065Notes

Reaction equation

HRID 1170065 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].C([O-])([O-])=O.[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>COCCO>[CH2:19]([O:12][C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 16043Tert-Butylhydroquinone

Product 1

HCID 12423646HCID 12423646, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a stirred solution of t-butyl hydroquinone (1.0 Kg) in 2-methoxy ethanol (2.0 L), was charged K2CO3 (2.0 Kg) portionwise under nitrogen atmosphere and the mixture refluxed. Benzyl chloride (0.762 L) was added dropwise at reflux temperature and heated further for 1.5 hr. The progress of the reaction was monitored on TLC. The reaction mixture was cooled and added DM Water (6.0 L). The uppermost oily layer was separated, dissolved in ethyl acetate (3.4 L), and washed with DM water (3.4 L×3). The uppermost oily layer was separated, dried over sodium sulfate and evaporated to dryness to give the crude title compound (1.5 Kg). The crude product was employed in the next step without further purification,

Workup

  1. temperaturethe mixture refluxed
  2. temperatureat reflux temperature
  3. temperatureheated further for 1.5 hr
  4. temperatureThe reaction mixture was cooled
  5. customThe uppermost oily layer was separated
  6. dissolutiondissolved in ethyl acetate (3.4 L)
  7. washwashed with DM water (3.4 L×3)
  8. customThe uppermost oily layer was separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-af631e3ece794fdd851f76755404db6f
Source dataset
uspto-grants-2010_11
Patent number
US07825257B1

Reaction notes

Loading…