p-Toluenesulfonic acid → HCID 13557855, compound

HRID 1154064Notes

Reaction equation

HRID 1154064 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[CH3:12][C:13]1([CH3:22])[C:15]2(CCC(C)=CC2)[O:14]1.[OH-:23].[Na+]>CO>[CH3:11][C:1]1[CH2:6][CH2:5][C:4]([C:13]([O:14][CH3:15])([CH3:22])[CH3:12])([OH:23])[CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 1073031-Oxaspiro[2.5]oct-5-ene, 2,2,6-trimethyl-

Product 1

HCID 13557855HCID 13557855, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 0.8 g of p-toluenesulfonic acid in 125 ml of methanol held at 3°-5° C. was added dropwise over 0.5 hour a solution of 15.2 g of 2,2,6-trimethyl-1-oxaspiro(2.5)oct-5-ene in 25 ml of methanol. After an additional 2 hours at 5° C. and 2 hours at 5°-20° C., the mixture was treated with 2 ml of 15% sodium hydroxide and concentrated at a water pump at below 60° C. The residue was dissolved in methylene chloride, washed, dried and Claisen-distilled to give 15.6 g of the desired product, b.p. 70° C. (0.2 mm).

Workup

  1. customheld at 3°-5° C.
  2. concentrationconcentrated at a water pump at below 60° C
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed
  5. customdried
  6. distillationClaisen-distilled

Sources & evidence

ORD record
ord-cbe7d94cf4194c19ba8a822498a5ca39
Source dataset
uspto-grants-1984_12
Patent number
US04487945

Reaction notes

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