Veratrole → HCID 14028056, compound

HRID 876199Notes

Reaction equation

HRID 876199 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[CH:11]1([C:16](O)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1>>[CH:11]1([C:16]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:9][CH3:10])[CH:5]=2)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 7043VeratroleHCID 18840Cyclopentanecarboxylic acid

Product 1

HCID 14028056HCID 14028056, compoundYield 116.1%

Conditions

Temperature
60 °C

Procedure

To polyphosphoric acid (76 g) was added 1,2-dimethoxybenzene (7.9 g, 0.057 mol) followed by cyclopentanecarboxylic acid (9.8 g, 0.086 mol). The mixture was stirred at 60° C. during 24 hours then cooled down to −5° C. and quenched by the addition of 200 ml ice/water followed by 100 ml of ether. After stirring at room temperature for 3 hours, the two layers were separated and the aqueous phase extracted with three 100 ml portions of ether. The two ethereal phases were combined, washed with 50 ml of NaOH and 50 ml of brine and dried over MgSO4. Filtration and concentration gave 15.5 g of dark brown oil. This oil was purified by vacuum distillation (180-190° C., 0.03 mbar) through a short path to give 11.8 g (88%) of a white solid.

Workup

  1. temperaturethen cooled down to −5° C.
  2. customquenched by the addition of 200 ml ice/water
  3. stirringAfter stirring at room temperature for 3 hours
  4. customthe two layers were separated
  5. extractionthe aqueous phase extracted with three 100 ml portions of ether
  6. washwashed with 50 ml of NaOH and 50 ml of brine
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-f0c864a659be42fca585848a57489c4f
Source dataset
uspto-grants-2015_03
Patent number
US08987188B2

Reaction notes

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