Acetic Anhydride → HCID 57772117, compound

HRID 1882318Notes

Reaction equation

HRID 1882318 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[O:14][CH3:15].[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][C:17](=[O:19])[CH3:18])=[CH:8][C:7]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 17604238HCID 17604238, compound

Product 1

HCID 57772117HCID 57772117, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (4-Hydroxymethyl-2-methoxy-phenoxy)-acetic acid methyl ester 72 (40 grams, 177 mmol), Acetic anhydride (80 mL) and pyridine (4 mL) was refluxed for 4 hours. Reaction mixture was poured in to ice water (200 mL) and crude 73 was extracted into chloroform, dried over Na2SO4, and distilled. The crude was vacuum distilled to give pure 73 (30 grams, 64%) as a color less liquid, Bp15 210° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 2.08 (s, 3H, O═C—CH3), 3.78 (s, 3H, ester), 3.90 (s, 3H, OCH3), 4.65 (s, 2H, OCH2), 5.00 (s, 2H, CH2), 6.76 (d, 1H, Ar), 6.80 (d, 2H, Ar), 6.85 (dd, 1H, Ar).

Workup

  1. customReaction mixture
  2. extractionwas extracted into chloroform
  3. dry with materialdried over Na2SO4
  4. distillationdistilled
  5. distillationdistilled

Sources & evidence

ORD record
ord-a22084872b4344ccba02475296d772d3
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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