Veratrole → HCID 59819744, compound

HRID 1629959Notes

Reaction equation

HRID 1629959 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[CH3:11][C:12]([CH3:17])=[CH:13][C:14](Cl)=[O:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:4][O:3][C:2]1[CH:5]=[C:6]([C:14](=[O:15])[CH:13]=[C:12]([CH3:17])[CH3:11])[CH:7]=[CH:8][C:1]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7043VeratroleHCID 1023943-Methyl-2-butenoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59819744HCID 59819744, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask equipped with a stir bar and nitrogen inlet was charged with veratrole (2.5 mL, 20 mmol), 3,3-dimethyl acryloyl chloride (2.2 mL, 20 mmol) and dry CH2Cl2, (100 mL). The solution was cooled to 0° C. and AlCl3 (2.6 g, 20 mmol) was added portionwise. On completion of addition, the cooling bath was removed and the reaction was allowed 3 h. TLC showed consumption of SM. It was added to saturated NH4Cl (100 mL) and stirred vigourously for 15 min. The phases were separated and the CH2Cl2 phase was washed with saturated Na2CO3 (100 mL), washed with brine, (100 mL), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The material was used as is in the next step. Amount obtained: 4.3 g, 19.5 mmol, 98% yield. LC-MS (ESI) m/e 221 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.02 (s, 3H) 2.20 (s, 3H) 3.96 (s, 6H) 6.73 (s, 1H) 6.89 (d, J=8.20 Hz, 1H) 7.53-7.60 (m, 2H). Step 2

Workup

  1. customA round bottom flask equipped with a stir bar and nitrogen inlet
  2. additionOn completion of addition
  3. customthe cooling bath was removed
  4. customconsumption of SM
  5. additionIt was added to saturated NH4Cl (100 mL)
  6. customThe phases were separated
  7. washthe CH2Cl2 phase was washed with saturated Na2CO3 (100 mL)
  8. washwashed with brine, (100 mL)
  9. dry with materialdried (Na2SO4)
  10. customthe solvent was evaporated under reduced pressure
  11. customAmount obtained

Sources & evidence

ORD record
ord-b2813672b3574e42ab0b1d180638f866
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

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