Sodium Bicarbonate → HCID 14537117, compound

HRID 2165193Notes

Reaction equation

HRID 2165193 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[O:32]C1CCCCO1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[OH:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[OH:32]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 14537116HCID 14537116, compound

Product 1

HCID 14537117HCID 14537117, compoundYield 125.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The 2-(12-tetrahydropyran-2-yloxydodeca-5,10-diynyl-1-(tetrahydropyran-2-yloxy)-4-methoxynaphthalene (0.396 g) is dissolved in 50% methanol/tetrahydrofuran (5 ml) and para-toluenesulfonic acid monohydrate (39 mg) is added. The mixture is heated to 60° C. for 35 minutes at which time TLC indicates complete reaction. After cooling, solid sodium bicarbonate is added, and the solvent is evaporated under reduced pressure. The residue is taken up in ethyl acetate and washed with water and brine, dried with magnesium sulfate, filtered, and concentrated to provide 0.335 g of a yellow oil.

Workup

  1. customTLC indicates complete reaction
  2. temperatureAfter cooling
  3. customthe solvent is evaporated under reduced pressure
  4. washwashed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5f306ed614cb4e19aa848462604e9c21
Source dataset
uspto-grants-1990_07
Patent number
US04939169

Reaction notes

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