Hydrochloric Acid → HCID 84731861, compound

HRID 629477Notes

Reaction equation

HRID 629477 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].[Cl-].[Mg+2].[Cl-].[CH2:14]=[O:15].Cl>ClC(Cl)C.C(N(CC)CC)C>[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH:14]=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5360315Magnesium ChlorideHCID 401517632-Fluoro-3-methoxyphenol

Product 1

HCID 84731861HCID 84731861, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-fluoro-3-methoxyphenol (22.0 g) and triethylamine (93.9 g) in dichloroethane (250 mL) was added magnesium chloride (71.7 g), and the mixture was stirred at 40° C. for 1 hr. To this mixture was added paraformaldehyde (46.5 g), and the mixture was stirred for 16 hr. The reaction solution was allowed to be cooled to room temperature, 1N hydrochloric acid was added thereto, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by combi flash (petroleum ether/ethyl acetate) to give the title compound (26.0 g).

Workup

  1. stirringthe mixture was stirred for 16 hr
  2. temperatureto be cooled to room temperature
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by combi flash (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-2ab485a679154d62964a95918073ed37
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

Loading…