Trifluoroacetic acid → HCID 18765814, compound

HRID 1733804Notes

Reaction equation

HRID 1733804 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[C:4]([OH:11])[C:3]=1[CH3:12].[OH-].[Na+].C([O:19][C:20](=[O:23])[CH2:21]Br)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[CH3:1][C:2]1[C:3]([CH3:12])=[C:4]([O:11][CH2:21][C:20]([OH:23])=[O:19])[C:5]([CH3:10])=[C:6]([CH3:9])[C:7]=1[OH:8]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 136346Durohydroquinone

Product 1

HCID 18765814HCID 18765814, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 20 mL of CH2Cl2, 20 mL H2O, 415 mg (1 eq) of tetramethylhydroquinone (D), 200 mg of NaOH, 540 mg (1.1 eq) of t-butylbromoacetate, 760 mg of C were stirred at room temperature, under argon, for 12 hr. Initially, D was not completely soluble, but with time, in 1 hr, it completely dissolved. After 12 hr, acid was added to bring the pH to 7.0, 200 mL of CH2Cl2 was added, and the reaction mixture was extracted with brine (4×200 mL), dried over Na2SO4, and evaporated under reduced pressure to yield crude product. 5 mL of TFA was added to the crude product, and the mixture was stirred for 1 hr. TFA was evaporated and the crude product charged on silica gel (230-400 mesh, CH2Cl2 -EtOAc, 2:1) to yield 270 mg (49%) of product 27.

Workup

  1. waitwith time, in 1 hr
  2. dissolutionit completely dissolved
  3. waitAfter 12 hr
  4. additionacid was added
  5. additionwas added
  6. extractionthe reaction mixture was extracted with brine (4×200 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated under reduced pressure
  9. customto yield crude product
  10. stirringthe mixture was stirred for 1 hr
  11. customTFA was evaporated
  12. additionthe crude product charged on silica gel (230-400 mesh, CH2Cl2 -EtOAc, 2:1)

Sources & evidence

ORD record
ord-5b0c79ec41e245bd9e06007179cc9726
Source dataset
uspto-grants-1996_07
Patent number
US05532138

Reaction notes

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