Hydrochloric Acid → HCID 57320364, compound

HRID 2081962Notes

Reaction equation

HRID 2081962 reaction equation
[C:1]([C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:20][C:21]1[CH:22]=[C:23]([OH:28])[C:24](=[CH:26][CH:27]=1)O.Cl>C1C=CC=CC=1.C(OCC)C>[CH3:20][C:21]1[CH:27]=[CH:26][C:24]2[O:8][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:28][C:23]=2[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99584-MethylcatecholHCID 15349Ethyl benzoylformateHCID 24819Phosphorus pentachloride

Product 1

HCID 57320364HCID 57320364, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl benzoylformate (520 mg, 2.92 mmoL) in dry benzene 5 mL) was added PCl5 (608 mg, 1.0 equiv). After stirring at reflux for 16 h TLC analysis indicated that all the starting material appeared consumed. The solvent was removed in vacuo and the crude dichloride (Rf=0.61 6:1 hexane/ethyl acetate) was mixed with 4-methyl-catechol (724 mg 2.0 equiv) and heated to 175° C. until HCl evolution ceased (ca. 20 min). The mixture was cooled to rt and the glue-like material was dissolved in diethyl ether and washed several times with 1N NaOH and then brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo and the residue was chromatographed on a silica column eluting with hexane/ethyl acetate (20:1). Removal of the solvent afforded 130 mg (16%) of the titled compound. Rf=0.57 (6:1 hexane/ethyl acetate).

Workup

  1. temperatureat reflux for 16 h TLC analysis
  2. customappeared consumed
  3. customThe solvent was removed in vacuo
  4. custom(ca. 20 min)
  5. washwashed several times with 1N NaOH
  6. dry with materialThe organic was dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customthe residue was chromatographed on a silica column
  9. washeluting with hexane/ethyl acetate (20:1)
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-8abe86b639844c168e8f0e37345c8a74
Source dataset
uspto-grants-1993_02
Patent number
US05187159

Reaction notes

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