Dimethylformamide → HCID 56973356, compound

HRID 1878318Notes

Reaction equation

HRID 1878318 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1>C(OC)(C)(C)C>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)[C:3]=1[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 697091-(2-Hydroxy-6-methoxyphenyl)ethan-1-oneHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 56973356HCID 56973356, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
35 °C

Procedure

1-(2-Hydroxy-6-methoxyphenyl)ethanone (1300 g, 7.82 mol) and dimethylformamide (10.4 L) are added to a 22 L flask and stirred to obtain a solution. Potassium carbonate (2700 g, 19.54 mol) is added in portions, then stirred for at least 30 min. Using an addition funnel, 4-methoxybenzyl chloride (14700 g, 9.39 mol) is added dropwise over 2.5 h to the mixture while maintaining the temperature <30° C. The reaction mixture is warmed to 35° C. and that temperature is held for 12 h. The reaction conversion is monitored by HPLC and deemed complete after 13 h at 35° C. The slurry is filtered and the resulting solids washed with dimethylformamide (1 L). Extractive work-up of the filtrate with ethyl acetate and water, followed by concentration, provided a waxy yellow solid. To the waxy yellow solid is added methyl t-butyl ether (2.6 L). The resulting slurry is agitated. The now free flowing slurry is filtered and washed with methyl t-butyl ether (1 L). The white solid is vacuum dried yielding 1539 grams (69%) of the title compound. mp 105-107° C.

Workup

  1. customto obtain a solution
  2. stirringstirred for at least 30 min
  3. temperaturewhile maintaining the temperature <30° C
  4. waitdeemed complete after 13 h at 35° C
  5. filtrationThe slurry is filtered
  6. washthe resulting solids washed with dimethylformamide (1 L)
  7. concentrationExtractive work-up of the filtrate with ethyl acetate and water, followed by concentration
  8. customprovided a waxy yellow solid
  9. stirringThe resulting slurry is agitated
  10. filtrationis filtered
  11. washwashed with methyl t-butyl ether (1 L)
  12. customdried

Sources & evidence

ORD record
ord-825bb0ba17654a1bbb6ca454cb39d210
Source dataset
uspto-grants-2012_11
Patent number
US08314108B2

Reaction notes

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