Bisphenol A → HCID 117689785, compound

HRID 705325Notes

Reaction equation

HRID 705325 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24]1[O:26][C@@H:25]1[CH2:27][OH:28].[Cl-].[NH4+]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:24][C@H:25]([OH:26])[CH2:27][OH:28])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6623Bisphenol AHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 5460455(+)-Glycidol

Product 1

HCID 117689785HCID 117689785, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of bisphenol A (10 g, 43.84 mmol, 1.0 equiv) in anhydrous dimethyl formamide (35 mL) at rt was added K2CO3 (9.1 g, 65.76 mmol, 1.5 equiv), and the mixture was stirred for 20 min under argon atmosphere. R(+) glycidol (3.8 mL, 56.99 mmol, 1.3 equiv) was added and the mixture was stirred for 5 h at 70-80° C. A saturated solution of ammonium chloride (10 mL) was added to the resulting orange-brown solution at room temperature. The mixture was extracted with ethyl acetate (3×15 mL). The organic layer was washed with deionized water (10 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 40% to 90% ethyl acetate in hexane) to provide the title compound (3.77 g, 28%) as a clear foam.

Workup

  1. stirringthe mixture was stirred for 5 h at 70-80° C
  2. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
  3. washThe organic layer was washed with deionized water (10 mL)
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography on silica gel (eluent: 40% to 90% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-32dffde7f35a41daa8510ede895baf07
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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