Sulfuric Acid → HCID 13563150, compound

HRID 1761371Notes

Reaction equation

HRID 1761371 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([O:10][C@@H:11]([CH3:15])[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:17][C:18](=[CH2:20])[CH3:19].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[C:1]1([CH3:16])[CH:2]=[CH:3][C:4]([S:7]([O:10][C@@H:11]([CH3:15])[C:12]([O:14][C:18]([CH3:20])([CH3:19])[CH3:17])=[O:13])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 10340Sodium CarbonateHCID 12761562(2S)-2-[(4-Methylbenzene-1-sulfonyl)oxy]propanoic acid

Product 1

HCID 13563150HCID 13563150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 2(S)-(p-toluenesulfonyloxy)propionic acid (4.4 g) to a cold solution of 10ml of isobutylene and 0.4 ml of concentrated sulfuric acid in 30 ml of methylene chloride in a pressure vessel, seal, and agitate at room temperature for 48 hours. Pour into 50 ml of 15% sodium carbonate solution, dry over magnesium sulfate and concentrate to obtain t-butyl 2(S)-(p-toluenesulfonyloxy)propionate as an oil (NMRδ1.37). Distilled material (Kugelrohr, 120°) has [α]D26 =-45.9° (EtOH, c=1).

Workup

  1. customseal
  2. dry with materialdry over magnesium sulfate
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-20c0156c6a884edea955d049a6ffc02c
Source dataset
uspto-grants-1989_05
Patent number
US04826816

Reaction notes

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