Veratrole → HCID 59819740, compound

HRID 1629964Notes

Reaction equation

HRID 1629964 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[Cl:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15]>>[Cl:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14]([C:7]1[CH:6]=[CH:5][C:2]([O:3][CH3:4])=[C:1]([O:9][CH3:10])[CH:8]=1)=[O:15]

Participants

3

Reactant 2

HCID 7043VeratroleHCID 613453-Chloro-2,2-dimethylpropanoyl chloride

Product 1

HCID 59819740HCID 59819740, compoundYield 93%

Conditions

Temperature
70 °C

Procedure

A 50 mL round bottom flask equipped with a stir bar was charged with veratrole (1.3 mL, 10 mmol) and 3-chloropivaloyl chloride (1.4 g, 10 mmol). To this mixture was added polyphosphoric acid (20 g). The mixture was heated at 70° C. for 2 h. [The progress of the reaction was followed by removing an aliquot for mini workup and NMR analysis.] The material was added to a mixture of ice water (100 mL)/EtOAc (100 mL) and stirred until the polyphosphoric acid had dissolved. The phases were separated and the EtOAc phase was washed with sat. NaHCO3 (100 mL), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The material was used as is in the next step. Amount obtained: 2.4 g, 9.3 mmol, 93% yield. LC-MS (ESI) m/e 257 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.51 (s, 6H) 3.83 (s, 2H) 3.93 (s, 3H) 3.95 (s, 3H) 6.87 (d, J=8.44 Hz, 1H) 7.37 (d, J=1.95 Hz, 1H) 7.48 (dd, J=8.42, 1.98 Hz, 1H). Step 2

Workup

  1. customA 50 mL round bottom flask equipped with a stir bar
  2. customby removing an aliquot for mini workup and NMR analysis
  3. addition] The material was added to a mixture of ice water (100 mL)/EtOAc (100 mL)
  4. dissolutionhad dissolved
  5. customThe phases were separated
  6. washthe EtOAc phase was washed with sat. NaHCO3 (100 mL)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customAmount obtained

Sources & evidence

ORD record
ord-f1841c6d924b485a8d1a50a457fd1ce5
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

Loading…