Hydrochloric Acid → 2-(2,3-Difluoro-4-(2-hydroxyethyl)phenoxy)acetaldehyde

HRID 471169Notes

Reaction equation

HRID 471169 reaction equation
Cl.C([O:4][CH:5](OCC)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[C:10]([F:17])[C:9]=1[F:18])C>O1CCOCC1.O>[F:18][C:9]1[C:10]([F:17])=[C:11]([CH2:14][CH2:15][OH:16])[CH:12]=[CH:13][C:8]=1[O:7][CH2:6][CH:5]=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579889892-(4-(2,2-Diethoxyethoxy)-2,3-difluorophenyl)ethanol

Product 1

HCID 866367532-(2,3-Difluoro-4-(2-hydroxyethyl)phenoxy)acetaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Concentrated hydrochloric acid (5 mL) was added to a solution of 2-(4-(2,2-diethoxyethoxy)-2,3-difluorophenyl)ethanol (example 77, step c) (0.49 g) in 1,4-dioxane (10 mL) and the resulting mixture was stirred for 1 h. The mixture was carefully diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organics were washed with water (50 mL) and brine (50 mL), dried over sodium sulphate, filtered and evaporated to give the subtitled compound, which was used directly. Yield 0.31 g.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d9371c8a2384405bb422374284e2c1fb
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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