Methanol → 2-(4-Fluorophenoxy)acetaldehyde

HRID 2083519Notes

Reaction equation

HRID 2083519 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 1.4M 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-31e599178ca14f6787f84effe67ffe62
Source dataset
uspto-grants-1978_04
Patent number
US04085272

Reaction notes

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