Bicarbonate Ion → HCID 9948616, compound

HRID 2292882Notes

Reaction equation

HRID 2292882 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:20])[CH2:17][S:18][CH3:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:29])C=1.C(=O)(O)[O-]>C(Cl)Cl>[C:12]([C:9]1[CH:8]=[C:7]([C:16](=[O:20])[CH2:17][S:18]([CH3:19])=[O:29])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 70297m-Chloroperbenzoic acidHCID 21480178HCID 21480178, compound

Product 1

HCID 9948616HCID 9948616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(methylsulfanyl)ethanone (15.00 g, 50.94 mmol) is dissolved in CH2Cl2 (100 mL) in a flame-dried flask under argon then cooled in an ice/H2O bath. mCPBA (85%, 10.45 g, 51.47 mmol) is added carefully, generating some gas evolution of H2. The reaction is stirred for 1.75 h while maintaining the bath temperature until the last 20 minutes when the bath is allowed to warm. The reaction is then poured into saturated bicarbonate, separated and extracted with 2× CH2Cl2. The organics are concentrated on a rotavap then dried under vacuum (being careful of foaming). This gives a light tan foam which is purified by flash chromatography on silica with 1.6 L 27.5% acetone in hexanes then 100% acetone. A white solid is obtained which can be crystallized with EtOAc/hexanes with refrigeration to give white crystals, mp=143.6°-144.9° C.

Workup

  1. temperaturethen cooled in an ice/H2O bath
  2. temperaturewhile maintaining the bath temperature until the last 20 minutes when the bath
  3. temperatureto warm
  4. customseparated
  5. extractionextracted with 2× CH2Cl2
  6. concentrationThe organics are concentrated on a rotavap
  7. customthen dried under vacuum (being careful of foaming)
  8. customThis gives a light tan foam which
  9. customis purified by flash chromatography on silica with 1.6 L 27.5% acetone in hexanes
  10. customA white solid is obtained which
  11. customcan be crystallized with EtOAc/hexanes with refrigeration
  12. customto give white crystals, mp=143.6°-144.9° C.

Sources & evidence

ORD record
ord-014945084ff443aabdf15bd978de0588
Source dataset
uspto-grants-1997_11
Patent number
US05684204

Reaction notes

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