Hydrochloric Acid → HCID 86733541, compound

HRID 1657973Notes

Reaction equation

HRID 1657973 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][CH:21]([CH3:23])[CH3:22])=[O:19].Cl.C(=O)([O-])[O-].[Na+].[Na+].[S:31]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)([O-:34])(=[O:33])=[O:32]>N1C=CC=CC=1>[C:38]1([CH3:39])[CH:37]=[CH:36][C:35]([S:31]([OH:34])(=[O:32])=[O:33])=[CH:41][CH:40]=1.[OH:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 85570p-ToluenesulfonateHCID 86733540HCID 86733540, compound

Product 1

HCID 86733541HCID 86733541, 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 1.00 g. (5.8 mm.) of isopropyl 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, sodium carbonate till neutral and dried over potassium carbonate. Evaporation of the solvent produced 1.32 g. (70% of theory) of crude tosylate.

Workup

  1. dry with materialdried over potassium carbonate
  2. customEvaporation of the solvent
  3. customproduced 1.32 g

Sources & evidence

ORD record
ord-3ce3ea93aefa46e29e39db5cfa09756f
Source dataset
uspto-grants-1976_06
Patent number
US03962354

Reaction notes

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