Methanol → 2-(4-Fluorophenoxy)acetaldehyde

HRID 1449264Notes

Reaction equation

HRID 1449264 reaction equation
C(O[O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1CC)(=O)C.[H-].C([Al+]C[CH:22]([CH3:24])C)C(C)C.C[OH:26].O>C1(C)C=CC=CC=1>[F:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:24][CH:22]=[O:26])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 88767291Ethyl-p-fluorophenoxy acetate

Product 1

HCID 110518692-(4-Fluorophenoxy)acetaldehydeYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 1.98 g (10 mmoles) of ethyl-p-fluorophenoxy acetate (Example 155) in 15 ml of dry toluene, cooled to -78 ° C., under argon, is added, dropwise over 30 minutes, 8 ml of a 1.4 M solution of diisobutylaluminum hydride in toluene (11 mmoles). The mixture is stirred for 2 hours at -78° C., 1 ml of methanol is added, followed by 5 ml of water, dropwise. The gel formed is filtered through Celite and washed with 100 ml of ether, portionwise. The organic phase is separated, washed twice with 25 ml of a saturated brine solution, dried with magnesium sulfate, filtered, and evaporated. The oil obtained is distilled at 71°-73° C. (0.1 mm) to give 600 mg (45%) of the subject product as a colorless liquid.

Workup

  1. additionis added, dropwise over 30 minutes
  2. customThe gel formed
  3. filtrationis filtered through Celite
  4. washwashed with 100 ml of ether
  5. customThe organic phase is separated
  6. washwashed twice with 25 ml of a saturated brine solution
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe oil obtained
  11. distillationis distilled at 71°-73° C. (0.1 mm)

Sources & evidence

ORD record
ord-8a7227ac844740fc8639d8d0ab730db5
Source dataset
uspto-grants-1980_02
Patent number
US04189597

Reaction notes

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