Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 14852605, compound

HRID 1031590Notes

Reaction equation

HRID 1031590 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][CH3:23].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[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][CH3:23]

Participants

6

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53675302,4-Dodecadienal, (2E,4E)-HCID 14374506HCID 14374506, compound

Product 1

HCID 14852605HCID 14852605, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Methyl 5,6-dihydroxyhexanoate (0.32 g, 2.0 mmol), 2E,4E-dodecadienal and catalytic pyridinium p-toluenesulfonate (PPTS) were refluxed in 10 ml of benzene for 39 hours with a Dean-Stark trap. Molecular sieves were added after 19 hours. The reaction mixture was cooled, filtered and concentrated. Flash chromatography on silica gel with 25:1 hexane/ethyl acetate as eluent gave the product (0.10 g, 0.31 mmol), 15%.

Workup

  1. additionMolecular sieves were added after 19 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-decf965ed492423db1c4588f8996a937
Source dataset
uspto-grants-1990_09
Patent number
US04954520

Reaction notes

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