Potassium Carbonate → HCID 50905028, compound

HRID 2406833Notes

Reaction equation

HRID 2406833 reaction equation
[OH:1][C:2]1[C:10]([CH2:11][CH2:12][CH3:13])=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.Br[CH2:15][C:16]#[C:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:1][C:2]1[C:10]([CH2:11][CH2:12][CH3:13])=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1)[C:16]#[C:17][CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 57217791HCID 57217791, compound

Product 1

HCID 50905028HCID 50905028, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Hydrogenation: the crude melted product was charged to an autoclave and diluted with 100 mL of isopropyl alcohol. 1.55 g of 5% Pd/C were added, and after flushing with nitrogen, the hydrogenation was carried out at 65° C. and 6 bar of H2 for 6 hrs. The mixture was cooled to room temperature and filtered on a celite pad to remove the catalyst. The organic solution was evaporated u.v. (20° C./21 mbar) and the residue distilled at 104°-112° C./0.1 mbar. 61 g of 5-hydroxy-6-propyl benzo[1.3]dioxole were obtained. Following the same procedure as in Example 3 c), 61 g. of 5-hydroxy-6-propyl benzo[1.3]dioxole were reacted with 45.9 g (0.34 moles) of 1-bromo-2-butyne and 47.7 g (0.34 moles) of anhydrous potassium carbonate in 250 ml of acetone. The filtrate in evaporated u.v. (20° C./ 21 mbar) and 69.1 g of 5-(but-2-ynyloxy)-6-propyl-benzo[1.3]dioxole were obtained (purity 75.5%).

Sources & evidence

ORD record
ord-6d655b0f474146a7ae20bc9d754edff6
Source dataset
uspto-grants-2014_08
Patent number
US08809389B2

Reaction notes

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