p-Toluenesulfonic acid → HCID 20157034, compound

HRID 986699Notes

Reaction equation

HRID 986699 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[Br:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([O:19][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][O:29]3)=[O:18])=[CH:15][C:14]=2[Br:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 13338867HCID 13338867, compound

Product 1

HCID 20157034HCID 20157034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In methylene chloride (30 ml) was dissolved 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoic acid (1.35 g). To the solution were added dihydropyran (0.9 ml) and p-toluene sulfonic acid.monohydrate (5 mg). The mixture was stirred at room temperature for 30 minutes, to which was further added methylene chloride (30 ml). The resulting solution was washed with an aqueous solution of sodium hydrogen carbonate and then with water, followed by drying with sodium sulfate. The solvent was evaporated off, and the residue was purified by means of a silica-gel column chromatography (Developing solvent: chloroform) to give 1.4 g of tetrahydropyranyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate as colorless oily substance.

Workup

  1. washThe resulting solution was washed with an aqueous solution of sodium hydrogen carbonate
  2. dry with materialby drying with sodium sulfate
  3. customThe solvent was evaporated off
  4. customthe residue was purified by means of a silica-gel column chromatography (Developing solvent: chloroform)

Sources & evidence

ORD record
ord-8c58465b37b6406998028a61b7e271bf
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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