Bicarbonate Ion → HCID 21480178, compound

HRID 2292881Notes

Reaction equation

HRID 2292881 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S:17][CH2:18][C:19](O)=[O:20].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.C(=O)(O)[O-]>CCOC(C)=O>[C:11]([C:7]1[CH:8]=[C:9]([C:19](=[O:20])[CH2:18][S:17][CH3:16])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 9845Trifluoroacetic anhydrideHCID 314052,6-Di-tert-butylphenolHCID 75551(Methylthio)acetic acid

Product 1

HCID 21480178HCID 21480178, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,6-di-t-butylphenol (1.7680 g, 8.66mmol) is placed in a flame dried RBF, and 2-(methylthio)acetic acid (0.80 mL, 9.19 mmol) is then added. This is then blanketed with argon and TFAA (1.30 mL, 9.20 mmol) is added via syringe at a fast rate. A small amount of CH2C12 is added to aid in mixing. The reaction quickly turns violet and darkens. It is followed by TLC using 10% EtOAc in hexanes. After 5 h, the reaction is carefully poured into 70 mL saturated bicarbonate and extracted with 2 portions of Et2O. The combined organics are washed with brine, filtered through cotton, dried over molecular sieves, then concentrated on a rotavap and dried under vacuum. This gives a white solid which can be crystallized from EtOAc/hexanes to give orange crystals, mp=108.5°-109.5° C.

Workup

  1. additionis then added
  2. additionis added via syringe at a fast rate
  3. additionA small amount of CH2C12 is added to aid
  4. additionin mixing
  5. customThe reaction quickly turns violet
  6. extractionextracted with 2 portions of Et2O
  7. washThe combined organics are washed with brine
  8. filtrationfiltered through cotton
  9. customdried over molecular sieves
  10. concentrationconcentrated on a rotavap
  11. customdried under vacuum
  12. customThis gives a white solid which
  13. customcan be crystallized from EtOAc/hexanes
  14. customto give orange crystals, mp=108.5°-109.5° C.

Sources & evidence

ORD record
ord-d4c1666d78e044d6997751c94ce77419
Source dataset
uspto-grants-1997_11
Patent number
US05684204

Reaction notes

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