Hydrochloric Acid → HCID 86733539, compound

HRID 1657970Notes

Reaction equation

HRID 1657970 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][C:18]([O:20][CH3:21])=[O:19].Cl.[S:23]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)([O-:26])(=[O:25])=[O:24]>N1C=CC=CC=1>[C:30]1([CH3:31])[CH:29]=[CH:28][C:27]([S:23]([OH:26])(=[O:24])=[O:25])=[CH:33][CH:32]=1.[OH:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 85570p-ToluenesulfonateHCID 15396982HCID 15396982, compound

Product 1

HCID 86733539HCID 86733539, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

p-Toluene sulfonyl chloride (1.425 g., 7.5 mm.) was added at 0°C to a solution of 1.00g. (6.95 mm.) of methyl cis 6-hydroxy-3-hexenoate in 2.37 g. of dry pyridine. The resulting mixture was stirred at 0°C for 4 hours. The crude product was poured on ice and concentrated hydrochloric acid, extracted with benzene, washed with 2N hydrochloric acid, sodium carbonate till neutral and dried over potassium carbonate. Evaporation of the solvent produced 1.425 g. (68% of theory) of crude tosylate.

Workup

  1. extractionextracted with benzene
  2. washwashed with 2N hydrochloric acid, sodium carbonate till neutral and
  3. dry with materialdried over potassium carbonate
  4. customEvaporation of the solvent
  5. customproduced 1.425 g

Sources & evidence

ORD record
ord-d1c5699f027c4d29bf116e78220a1a5e
Source dataset
uspto-grants-1976_06
Patent number
US03962354

Reaction notes

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