Hydrochloric Acid → 2-(4-(2-Hydroxyethyl)phenoxy)acetaldehyde

HRID 446375Notes

Reaction equation

HRID 446375 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])=[CH:10][CH:9]=1)C>O1CCOCC1.O>[OH:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH:5]=[O:4])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579889402-(4-(2,2-Diethoxyethoxy)phenyl)ethanol

Product 1

HCID 545162782-(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)phenyl)ethanol [Aromatic Intermediate 12, step a] (0.76 g) in 1,4-dioxane (10 mL) and the resulting mixture was stirred for 1 h. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic solutions were washed with water (50 mL) and brine (50 mL), then dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound, which was used directly. Yield 0.35 g.

Workup

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

Sources & evidence

ORD record
ord-6dbe817b94514ba4a3b3caa67a4ed022
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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