Benzyl Bromide → HCID 11781863, compound

HRID 1940218Notes

Reaction equation

HRID 1940218 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:9]([CH3:22])=[C:10]([CH3:21])[C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[C:19]=1[CH3:20].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH2:23]([O:7][C:8]1[C:9]([CH3:22])=[C:10]([CH3:21])[C:11]2[O:15][C:14]([CH3:16])([CH3:17])[C:13](=[O:18])[C:12]=2[C:19]=1[CH3:20])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10220089HCID 10220089, compound

Product 1

HCID 11781863HCID 11781863, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (720 g) is added to a solution of 5-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-one (453 g, 2.1 mol) in acetone (2 L). A solution of benzyl bromide (423 g, 2.5 mmol) in acetone (200 mL) is added portionwise over a period of 10 min. A slight exotherm is observed. After 3 hrs, the mixture is heated to reflux. After 39 hrs, TLC shows complete conversion to product. The mixture is cooled to 50° C. and filtered using 1.5 L of ethyl acetate to remove the solids from the flask. The solids are washed with ethyl acetate (1.5 L). The filtrate is concentrated. The resulting solids are dissolved in ethyl acetate (7 L). This solution is washed with water, dried (magnesium sulfate) and concentrated. The resulting solids are placed on a tray for air-drying. After 2 days, 5-benzyloxy-2,2,4,6,7-pentamethyl-2,3-d3-onenzofuran-3-one is collected (638g, 99%). mp=114° C.-115° C.

Workup

  1. temperaturethe mixture is heated to reflux
  2. waitAfter 39 hrs
  3. filtrationfiltered
  4. customto remove the solids from the flask
  5. washThe solids are washed with ethyl acetate (1.5 L)
  6. concentrationThe filtrate is concentrated
  7. dissolutionThe resulting solids are dissolved in ethyl acetate (7 L)
  8. washThis solution is washed with water
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated
  11. customfor air-drying
  12. waitAfter 2 days
  13. custom5-benzyloxy-2,2,4,6,7-pentamethyl-2,3-d3-onenzofuran-3-one is collected (638g, 99%)

Sources & evidence

ORD record
ord-0fd8a1d8768847adb1d093e11dbf9699
Source dataset
uspto-grants-1997_12
Patent number
US05698696

Reaction notes

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