Acetic Anhydride → HCID 57772117, compound

HRID 2405185Notes

Reaction equation

HRID 2405185 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-85d3a7403eb54e45b0dc9c5923283745
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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