Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 22128591, compound

HRID 1858802Notes

Reaction equation

HRID 1858802 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][CH2:11][CH2:12][O:13]C1CCCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22128473HCID 22128473, compound

Product 1

HCID 22128591HCID 22128591, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 9.5 g (33.6 mmol) of (RS)-2-[3-(2-methoxy-phenylsulphanyl)-propoxy]-tetrahydro-pyran and 1.0 g (4 mmol) of pyridinium toluene-4-sulphonate in 100 ml of methanol was heated to reflux for 2 hours. For the working-up, the solvent was distilled off under reduced pressure and then the residue was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic phase was subsequently dried over sodium sulphate and evaporated under reduced pressure. The 3-(2-methoxy-phenylsulphanyl)-propane-1-ol was obtained as a yellowish liquid in quantitative yield; MS: 198 (M)+. Reaction with mesyl chloride, effected according to a generally known procedure, yielded 3-(2-methoxy-phenylsulphanyl)-propyl methanesulphonate as a pale yellow liquid; MS: 276 (M)+.

Workup

  1. temperatureto reflux for 2 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution
  4. dry with materialThe organic phase was subsequently dried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-957c0f8358004592921de55da260df84
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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