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

HRID 470952Notes

Reaction equation

HRID 470952 reaction equation
Cl.C([O:4][CH:5](OCC)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1)C>CC(C)=O>[OH:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH:5]=[O:4])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57989210[4-(2,2-Diethoxy-ethoxy)-phenyl]-methanol

Product 1

HCID 544756782-(4-(Hydroxymethyl)phenoxy)acetaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2M HCl (4 mL) was added to a solution of (4-(2,2-diethoxyethoxy)phenyl)methanol (example 1, step g) (0.9 g) in acetone (20 mL) and the resulting mixture was stirred for 16 h at room temperature. The reaction was concentrated in vacuo and the resulting aqueous solution extracted with ethyl acetate (3×20 mL). The combined organic solutions were dried over magnesium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a clear gum, which was used directly in the next step. Yield 0.50 g.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionthe resulting aqueous solution extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic solutions were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c01224024f14403ba672b059cdde00e2
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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