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

HRID 470958Notes

Reaction equation

HRID 470958 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 (example 3, 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-c1cc1aff49664670afc56c256dc7dcfb
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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