Hydrochloric Acid → 4-Sulfanylphenyl methanesulfonate

HRID 2083701Notes

Reaction equation

HRID 2083701 reaction equation
C([S:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1)(=O)C.Cl>CO>[CH3:15][S:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([SH:4])=[CH:6][CH:7]=1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20357375S-{4-[(Methanesulfonyl)oxy]phenyl} ethanethioate

Product 1

HCID 135183004-Sulfanylphenyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

S-[4-(methanesulfonyloxy)phenyl] thioacetate (20.4 g., 0.083 mole) is dissolved in 150 ml. of warm (45° C.) methanol. Concentrated hydrochloric acid, 5 ml., is added and the solution is held at 45°-55° C. for 2 hours. The solution is then concentrated in vacuo to approximately 40 ml., taken up in 200 ml. of chloroform, washed with 50 ml. of water, dried over sodium sulfate and concentrated in vacuo to give 15.8 g. (93%) of the desired thiophenol as a white crystalline solid, m.p.=66°-68° C. (after recrystallization from carbon tetrachloride). Analysis calc. (found): C 41.2 (41.3); H 3.95 (4.03).

Workup

  1. addition, is added
  2. concentrationThe solution is then concentrated in vacuo to approximately 40 ml
  3. washof chloroform, washed with 50 ml
  4. dry with materialof water, dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give 15.8 g
  7. custom(93%) of the desired thiophenol as a white crystalline solid, m.p.=66°-68° C. (after recrystallization from carbon tetrachloride)

Sources & evidence

ORD record
ord-7cd070011c1c4e8b958fa46d44345b70
Source dataset
uspto-grants-1978_04
Patent number
US04086337

Reaction notes

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