p-Toluenesulfonic acid → 1,1-Dimethylethyl 2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetate

HRID 1608415Notes

Reaction equation

HRID 1608415 reaction equation
[OH:1][CH:2]([CH2:11][CH:12]([OH:21])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:22]1(C)[CH:27]=CC(S(O)(=O)=O)=C[CH:23]=1>CC(C)=O>[CH3:23][C:22]1([CH3:27])[O:1][CH:2]([CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5])[CH2:11][CH:12]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:21]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53722944t-Butyl 7-phenyl-3,5-dihydroxy-6-heptenoate

Product 1

HCID 538002911,1-Dimethylethyl 2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl 3,5-dihydroxy-7-phenyl-6-heptenoate (5.5 g, 19 mmol) in acetone (2.3 g, 40 mmol) was added a catalyic amount of p-toluenesulfonic acid. After stirring for 2 hours, the mixture had solidified and was dissolved in excess acetone and filtered through a pad of sodium carbonate. The excess acetone was removed in vacuo and the residue crystallized from isopropyl ether to give 3.4 g of the title compound; m.p.=91°-93° C.

Workup

  1. filtrationfiltered through a pad of sodium carbonate
  2. customThe excess acetone was removed in vacuo
  3. customthe residue crystallized from isopropyl ether

Sources & evidence

ORD record
ord-3b47065d311148e9ac4fc95736a2fa49
Source dataset
uspto-grants-1989_09
Patent number
US04870187

Reaction notes

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