Acetic Anhydride → HCID 14457928, compound

HRID 357539Notes

Reaction equation

HRID 357539 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N+:15]([O-])=[C:14]([CH3:19])[C:13]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:24]C(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:24][CH2:19][C:14]1[C:13]([CH3:20])=[C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH:16][N:15]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 14457927HCID 14457927, compound

Product 1

HCID 14457928HCID 14457928, compound

Procedure

A mixture comprising 6.5 g of 4-(2-benzyloxyethoxy-2,3-dimethylpyridine N-oxide and 56 ml of acetic anhydride was stirred at 80° to 90° C. for one hour and distilled to remove the acetic anhydride. The obtained residue was made weakly basic with an aqueous solution of sodium carbonate and extracted with methyl ethyl ketone. The extract was dried over magnesium sulfate and distilled to remove the methyl ethyl ketone. Thus, 7.0 g of 2-acetoxymethyl-4-(2-benzyloxyethoxy)-3-methylpyridine was obtained. This intermediate was dissolved in 90 ml of ethanol, followed by the addition of 1.43 g of sodium hydroxide. The obtained mixture was stirred at 40° C. for one hour, followed by the addition of water. The mixture was extracted with methyl ethyl ketone. The obtained extract was dried over magnesium sulfate to obtain 5.4 g of 4-(2-benzyloxyethoxy)-2-hydroxymethyl-3-methylpyridine.

Workup

  1. distillationdistilled
  2. customto remove the acetic anhydride
  3. extractionextracted with methyl ethyl ketone
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationdistilled
  6. customto remove the methyl ethyl ketone

Sources & evidence

ORD record
ord-afc34e4d31f04ef6b8331327d52cade2
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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