2,4-Di-tert-butylphenol → 2,4-Di-tert-butyl-6-[(2,6-dimethylphenyl)sulfanyl]phenol

HRID 272264Notes

Reaction equation

HRID 272264 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[S:8]Cl.[C:11]([C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=1[OH:25])([CH3:14])([CH3:13])[CH3:12]>>[C:11]([C:15]1[C:16]([OH:25])=[C:17]([S:8][C:2]2[C:3]([CH3:7])=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:10])[CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 73112,4-Di-tert-butylphenolHCID 14572051HCID 14572051, compound

Product 1

HCID 713615722,4-Di-tert-butyl-6-[(2,6-dimethylphenyl)sulfanyl]phenolYield 59%

Procedure

Under N2, 2.225 g m-xylene-2-sulfenyl chloride (12.9 mmol) were dissolved in 25 mL hexanes. Under air, a 100 mL 3-necked round-bottom flask was charged with stirbar and 2.64 g 2,4-di-tert-butylphenol (12.8 mmol), then reflux condenser with vacuum adapter and addition funnel were attached. The phenol was dried in vacuo for 20 minutes, then placed under N2 and immersed in an oil bath set at 100° C. The solution of m-xylene-2-sulfenyl chloride was then added via addition funnel and the reaction mixture refluxed overnight. Solvent had evaporated by morning, probably through a leaky joint. The resulting brown solid was ground up in mortar and pestle and recrystallized from ethanol, yielding 2.170 g cream-colored solid which melted at 101-102° C. A second, somewhat darker crop of 0.434 g was recovered from the mother liquor. Combined yield: 59% (based on 2,4-di-tert-butylphenol). 1H NMR (CDCl3), δ (ppm): 7.07-7.13 (m), 4H, Ar—H; 6.82 (d, J=2.4 Hz), 1H, Ar—H; 6.28 (s), 1H, OH; 2.41 (s), 6H, CH3; 1.38 (s), 9H, t-Bu; 1.13 (s), 9H, t-Bu.

Workup

  1. temperaturereflux condenser
  2. additionwith vacuum adapter and addition funnel
  3. dry with materialThe phenol was dried in vacuo for 20 minutes
  4. customimmersed in an oil bath
  5. customset at 100° C
  6. additionThe solution of m-xylene-2-sulfenyl chloride was then added via addition funnel
  7. temperaturethe reaction mixture refluxed overnight
  8. customSolvent had evaporated by morning, probably through a leaky joint
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-252542054abd49b4a2010c5c06fbd3c5
Source dataset
uspto-grants-2008_11
Patent number
US07456127B2

Reaction notes

Loading…