Bicarbonate Ion → 4-Methyl-α-phenylbenzeneacetic acid

HRID 1955733Notes

Reaction equation

HRID 1955733 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(O)[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-]>ClCCl.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 19072491HCID 19072491, compound

Product 1

HCID 158904-Methyl-α-phenylbenzeneacetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.49 g (5 mmol) of tert-butyl 2-(4-methyl-phenyl)-2-phenyl-2-hydroxy-acetate are stirred at room temperature in 60 ml of dichloromethane for 3 h with 6.3 ml (40 mmol) of triethylsilane and 12.6 ml (60 mmol) of trifluoroacetic acid. The mixture is diluted with 60 ml of water, adjusted to a pH of 2-3 with saturated aqueous bicarbonate solution and shaken. After removal of the organic phase, the aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried over sodium sulphate, filtered and concentrated. The product is chromatographed on silica gel 60 using 40-60 petroleum ether/ethyl acetate (6:4).

Workup

  1. customAfter removal of the organic phase
  2. extractionthe aqueous phase is extracted twice more with dichloromethane
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product is chromatographed on silica gel 60 using 40-60 petroleum ether/ethyl acetate (6:4)

Sources & evidence

ORD record
ord-1a4ca61b461740978abe5f035b1c67aa
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

Loading…