Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 14852592, compound

HRID 1031589Notes

Reaction equation

HRID 1031589 reaction equation
[OH:1][CH:2]([CH2:10][OH:11])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH:12](=O)/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH:13](/[CH:12]1[O:1][CH:2]([CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:10][O:11]1)=[CH:14]\[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5283371HCID 5283371, compoundHCID 14374506HCID 14374506, compound

Product 1

HCID 14852592HCID 14852592, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 5,6-dihydroxyhexanoate (0.32 g, 2.0 mmol),2E,4E -pentadecadienal (0.445 g, 2.0 mmol) and catalytic pyridinium p-toluene sulfonate (PPTS) were refluxed in 10 ml of benzene with a Dean Stark trap for 21 hours. The mixture was cooled, filtered, and concentrated. Flash chromatography with 25:1+20:1 hexane/ethyl acetate provided methyl 2-tetradeca-1E,-3E-dienyl-1, 3-dioxolane-4-butanoate as 21 mg of isomer B as a crystalline solid, 25 mg of isomer A, as a crystalline solid, and 68 mg of a mixture of A and B.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b556c862039345029c9b2423c5316db5
Source dataset
uspto-grants-1990_09
Patent number
US04954520

Reaction notes

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