Water → 4-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol

HRID 1250789Notes

Reaction equation

HRID 1250789 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][OH:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[CH2:13][OH:14].O.[OH-].[K+].S(OC)(O[CH3:22])(=O)=O>C1(C)C=CC=CC=1>[CH3:22][O:14][CH2:13][C:3]1[C:2]([F:1])=[C:7]([F:8])[C:6]([CH2:9][OH:10])=[C:5]([F:11])[C:4]=1[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl Sulfate3×HCID 14797Potassium Hydroxide3×HCID 40988352,3,5,6-Tetrafluoro-1,4-benzenedimethanol2×

Product 1

HCID 111721164-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcoholYield 100.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Into a reaction vessel that was charged nitrogen, 5.00 g (23.1 mmol) of 2,3,5,6-tetrafluoro-1,4-benzenedimethanol, 15.00 g of water and 1.30 g (23.1 mmol) of potassium hydroxide were charged subsequently, and heated to 60° C. with stirring. At this time, solid 2,3,5,6-tetrafluoro-1,4-benzenedimethanol was completely dissolved to be a clear solution. Then, a mixture of 15.0 g of toluene and 3.07 g (23.1 mmol) of dimethyl sulfate was added at 55±5° C. After stirring at 50±5° C. for 1.5 hours, 0.64 g (11.4 mmol) of potassium hydroxide and 1.51 g (12.6 mmol) of dimethyl sulfate were added. After 1.5 hours, 0.66 g (11.7 mmol) of potassium hydroxide and 1.51 g (12.6 mmol) of dimethyl sulfate were further added and stirred at the same temperature for 1.5 hours. Allowing the reaction mixture to cool to room temperature, the layers of the reaction mixture were separated and the water layer was extracted with 30 ml of ethyl acetate. The organic layers were combined, washed with 30 ml of water, concentrated, and dried under reduced pressure to give 5.22 g of crude 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol. The crude 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol was subjected to content analysis by GC internal standard method (Analytical method 1 given later). GC area percentage of the crude product: 87% of the objective compound, 4% of the starting compound and 8% of the by-product compound Content analysis by GC internal standard method: 85% of the objective compound and 86% of the yield of pure compound

Workup

  1. additionwere charged subsequently
  2. additionwas added at 55±5° C
  3. stirringAfter stirring at 50±5° C. for 1.5 hours
  4. stirringstirred at the same temperature for 1.5 hours
  5. temperatureAllowing the reaction mixture to cool to room temperature
  6. customthe layers of the reaction mixture were separated
  7. extractionthe water layer was extracted with 30 ml of ethyl acetate
  8. washwashed with 30 ml of water
  9. concentrationconcentrated
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9cc33ac525141d6996a991615b5e238
Source dataset
uspto-grants-2002_01
Patent number
US06339176B2

Reaction notes

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