Hydrochloric Acid → HCID 54133978, compound

HRID 970256Notes

Reaction equation

HRID 970256 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C[O:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>CCOCC>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 132454-Methoxy cinnamic acid

Product 1

HCID 54133978HCID 54133978, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

14 ml of dihydropyran was added dropwise to a mixture of 17.8 g of 4-methoxycinnamic acid, 0.34 g of 4-toluene sulphonic acid and 100 ml of diethyl ether under a nitrogen atmosphere. After one hour stirring the solution became transparent. 150 ml of ether was added and it was extracted with 200 ml of 5% of sodium hydroxide solution and evaporated using a rotary evaporator. The residue was mixed with 50 ml of ethanol and a solution of 8 g of KOH in 50 ml of water and was refluxed for 1 hour upon which a transparent solution was obtained. It was cooled with 150 g of crushed ice. Then 50 ml of HCl (2.5 N) was added dropwise to the solution until pH=4 upon which a solid precipitated. It was filtered off and washed with water. The product was dried in a dessicator over silica. 19.59 g (yield 79%) of a white solid was obtained.

Workup

  1. extractionit was extracted with 200 ml of 5% of sodium hydroxide solution
  2. customevaporated
  3. customa rotary evaporator
  4. additionThe residue was mixed with 50 ml of ethanol
  5. temperaturea solution of 8 g of KOH in 50 ml of water and was refluxed for 1 hour upon which a transparent solution
  6. customwas obtained
  7. customprecipitated
  8. filtrationIt was filtered off
  9. washwashed with water
  10. customThe product was dried in a dessicator over silica

Sources & evidence

ORD record
ord-b85d8d10ff604b65b0b1f5a9082fa148
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

Loading…