Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86743011, compound

HRID 1761786Notes

Reaction equation

HRID 1761786 reaction equation
[CH3:1]/[C:2](=[CH:10]\[CH2:11][CH2:12]/[C:13](/[CH3:23])=[CH:14]/[CH2:15][O:16]C1CCCCO1)/[CH2:3][CH2:4][CH:5]([OH:9])[CH2:6][C:7]#[CH:8].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[CH3:23]/[C:13](/[CH2:12][CH2:11]/[CH:10]=[C:2](\[CH3:1])/[CH2:3][CH2:4][CH:5]([OH:9])[CH2:6][C:7]#[CH:8])=[CH:14]\[CH2:15][OH:16]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86743012HCID 86743012, compound

Product 1

HCID 86743011HCID 86743011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.40 g of (E,E)-7,11-dimethyl-13-[(tetrahydro-2H-pyran-2-yl)oxy]-7,11-tridecadien-1-yn-4-ol and 1.50 g of pyridinium toluene-4-sulfonate in 200 ml of abs. ethanol is heated to 60° under argon for 2.5 hours. The reaction mixture is cooled and evaporated, and the residue is taken up in ether and water. After separating the organic phase the aqueous phase is extracted twice with ether and the combined organic phases are washed with 2N hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated. The yellow oil which remains behind as the residue is chromatographed on 400 g of silica gel, with elution being carried with hexane-ethyl acetate 25%→40%. In this manner there is obtained (E,E)-3,7-dimethyltrideca-2,6-dien-12-yn-1,10-diol as a yellowish oil. IR (film); 3350 (OH); 3305, 2118 (--C≡CH); 1667 (C=C); 1003, (OH). MS: 205 (1, (M--CH 2 OH)+); 203 (1, M--H2O--CH3)+); 105 (100); 93 (100).

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated
  3. customAfter separating the organic phase the aqueous phase
  4. extractionis extracted twice with ether
  5. washthe combined organic phases are washed with 2N hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customis chromatographed on 400 g of silica gel, with elution

Sources & evidence

ORD record
ord-c6cc539187d447d9933541925c0b5ecc
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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