Hydrochloric Acid → HCID 54722180, compound

HRID 2912Notes

Reaction equation

HRID 2912 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[C:7]([CH2:9][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([OH:19])[CH:13]=2)O)[O:6][C:5](=[O:20])[CH:4]=1.O1CCCC1.C1(C)C=CC=CC=1.C(OCC)=O.CO>C(O)=O>[OH:19][C:14]1[CH:13]=[C:12]([CH:10]=[CH:9][C:7]2[O:6][C:5](=[O:20])[CH:4]=[C:3]([OH:2])[CH:8]=2)[CH:17]=[CH:16][C:15]=1[OH:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 19688079Toluene ethyl formate methanolHCID 867523204-Hydroxy-6-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-2H-pyran-2-one

Product 1

HCID 54722180HCID 54722180, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2 ml 3N HCl was added to a suspension of 8.0 g (30 mmol) 4-hydroxy-6-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-2H-pyran-2-one VII and 300 ml tetrahydrofuran. The resulting clear solution was heated for 2-3 hours under reflux until it was no longer possible to detect starting material. (TLC control, mobile solvent: toluene/ethyl formate/methanol 5:4:1, 0.5% formic acid). After drying over sodium sulphate the solution was strongly evaporated (residual volume ca. 50 ml) and it was crystallized by admixing with ether. Yield 4.7 g (63%) hispidine II, melting point 232°-234° C. (decomp.) or melting point 253° C. (decomp; bunch of needles from toluene/ethyl formate).

Workup

  1. temperatureThe resulting clear solution was heated for 2-3 hours
  2. temperatureunder reflux until it
  3. dry with materialAfter drying over sodium sulphate the solution
  4. customwas strongly evaporated (residual volume ca. 50 ml) and it
  5. customwas crystallized

Sources & evidence

ORD record
ord-2778a9f71b614c56aa952dc1c3b7fac4
Source dataset
uspto-grants-1998_03
Patent number
US05731344

Reaction notes

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