O-Xylene → HCID 19922115, compound

HRID 1647975Notes

Reaction equation

HRID 1647975 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:19](=[O:21])[CH3:20].[CH3:22]OC(OC)N(C)C.C1(C)C(C)=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.CCOCC.C(O)C.CO>[C:13]1([CH2:12][O:11][C:6]2[CH:5]=[CH:4][C:3]3[C:19](=[O:21])[CH:20]=[CH:22][O:1][C:2]=3[C:7]=2[CH2:8][CH2:9][CH3:10])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

9

Reactant 4

HCID 7237O-XyleneHCID 78373Dimethylformamide dimethyl acetalHCID 521998p-Toluenesulfonic acid monohydrateHCID 2801568HCID 2801568, compound

Product 1

HCID 19922115HCID 19922115, compoundYield 87.5%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.09 g (10.88 mmol) of 1-[2-hydroxy-4-(phenylmethoxy)-3-propylphenyl]ethanone, 1.55 g (13 mmol) of dimethylformamide dimethyl acetal, and 2.7 mL of xylene was stirred and heated in a 120°-130° C. oil-bath as methanol was distilled out using a 3 in. Vigreux column, over a 2 hr period. The bath temperature was then raised to 150°-160° C. and the reaction mixture was stirred at this temperature for an additional 30 min. The mixture was cooled and concentrated at 60° C./high vacuum. To the viscous, red-brown, oily residue was added 2.48 g (13 mmol) of p-toluenesulfonic acid monohydrate and 25 mL of ethanol. The resulting solution was stirred and refluxed for 1.5 hr, then cooled and diluted with 100 mL of water. Work-up with ether in the usual manner gave a crude product which was purified by flash chromatography on silica gel, eluting with 1:1 hexane-ether. There was obtained 2.8 g (87.5%) of 7-(phenylmethoxy)-8-propyl-4H-1-benzopyran-4-one as a beige solid. An analytical specimen was obtained from another experiment by recrystallization from ethyl acetate-hexane, as a colorless solid, mp 87.5°-89° C.

Workup

  1. distillationwas distilled out
  2. temperatureThe bath temperature was then raised to 150°-160° C.
  3. stirringthe reaction mixture was stirred at this temperature for an additional 30 min
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated at 60° C./high vacuum
  6. stirringThe resulting solution was stirred
  7. temperaturerefluxed for 1.5 hr
  8. temperaturecooled
  9. customgave a crude product which
  10. customwas purified by flash chromatography on silica gel
  11. washeluting with 1:1 hexane-ether

Sources & evidence

ORD record
ord-08a1af88ba2a4e8db0352d26c6b9d1a4
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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