Hydrochloric Acid → HCID 14718897, compound

HRID 1085720Notes

Reaction equation

HRID 1085720 reaction equation
[CH3:1][O-:2].[Na+].[CH2:4]([O:6][CH2:7][C:8]1[C:15]([F:16])=[C:14](F)[C:11]([CH2:12][OH:13])=[C:10]([F:18])[C:9]=1[F:19])[CH3:5].O.Cl>CO.COCCOCCOC>[F:18][C:10]1[C:9]([F:19])=[C:8]([CH2:7][O:6][CH2:4][CH3:5])[C:15]([F:16])=[C:14]([O:2][CH3:1])[C:11]=1[CH2:12][OH:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium Methoxide2×HCID 14718895HCID 14718895, compound

Product 1

HCID 14718897HCID 14718897, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8150DiglymeSolvent

Conditions

Temperature
90 °C

Procedure

A solution of sodium methoxide (generated from 0.13 g sodium) in dry methanol (20 cm3) was added to a solution of 4-(ethoxymethyl)-2,3,5,6-tetrafluorobenzyl alcohol (1.2 g) in dry diglyme. The stirred reaction mixture was heated at 90° C. for a period of 4 hours, under an atmosphere of dry nitrogen, after which time a further portion of sodium methoxide (0.1 g) was added, and heating continued for a further 8 hours. After cooling to the ambient temperature the reaction mixture was poured into water, acidified with dilute aqueous hydrochloric acid, and extracted into ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulphate, and concentrated by evaporation of the solvent under reduced pressure. The brown residue was subjected to column chromatography on silica gel using hexane containing increasing amounts of diethyl ether (from 0% to 100%) by volume as eluent. The crude product thus obtained was gain subjected to chromatography on silica gel in a similar manner to give 2,3,5-trifluoro-4-(ethoxymethyl)-6-methoxybenzyl alcohol (0.3 g) as a pale yellow oil.

Workup

  1. customThe stirred reaction mixture
  2. temperatureheating
  3. temperatureAfter cooling to the ambient temperature the reaction mixture
  4. extractionextracted into ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  6. concentrationconcentrated by evaporation of the solvent under reduced pressure
  7. temperatureincreasing amounts of diethyl ether (from 0% to 100%) by volume as eluent
  8. customThe crude product thus obtained

Sources & evidence

ORD record
ord-f0d4c311723845b7b9e265fb9b107751
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Reaction notes

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