M-Cresol → HCID 21430249, compound

HRID 437115Notes

Reaction equation

HRID 437115 reaction equation
[CH:1]1[C:6](O)=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].C1([S:15]Cl)C=CC=CC=1.[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)(Cl)(Cl)Cl>[CH3:8][C:2]1[CH:1]=[C:6]([SH:15])[CH:5]=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 996Phenol2×HCID 11008040Benzenesulfenyl chloride

Product 1

HCID 21430249HCID 21430249, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 22.4 g. (0.21 mole) of m-cresol in 100 ml. of carbon tetrachloride is added dropwise with stirring, 30.0 g. (0.21 mole) of phenyl sulfenyl chloride at 0°-5° C. over a period of 30 minutes. The light pink solution is stirred overnight at room temperature and then concentrated in vacuo to give 44.8 g. of the impure phenol. The crude product is taken up in 100 ml. of 10% sodium hydroxide, and extracted twice with 50 ml. portions of ether, which are discarded. The basic solution is neutralized with concentrated hydrochloric acid and then extracted twice with 50 ml. portions of chloroform. The organic extracts are combined, dried over sodium sulfate and concentrated in vacuo to give 34.9 g. of yellow oil. Fractional distillation yields 19.9 g. (b.p. 125°-135° C./ 0.1 mm) of the desired phenol.

Workup

  1. stirringThe light pink solution is stirred overnight at room temperature
  2. concentrationconcentrated in vacuo
  3. customto give 44.8 g
  4. extractionof 10% sodium hydroxide, and extracted twice with 50 ml
  5. extractionextracted twice with 50 ml
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give 34.9 g
  9. distillationFractional distillation
  10. customyields 19.9 g

Sources & evidence

ORD record
ord-56e9ab0d2b2b4a5381a65b6b59f56a96
Source dataset
uspto-grants-1977_06
Patent number
US04029774

Reaction notes

Loading…