Acetic Anhydride → (4-Acetoxymethyl-phenoxy)-acetic Acid Methyl Ester

HRID 2405183Notes

Reaction equation

HRID 2405183 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][C:15](=[O:17])[CH3:16])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 690034Methyl 2-(4-hydroxymethylphenoxy)acetate

Product 1

HCID 20717763(4-Acetoxymethyl-phenoxy)-acetic Acid Methyl EsterYield 61.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (4-hydroxymethyl-phenoxy)-acetic acid methyl ester 69 (100 grams, 509 mmol), acetic anhydride (250 mL) and pyridine (20 mL) was refluxed for 4 hours. Reaction mixture was poured in to ice water (1000 mL) and crude 70 was extracted into chloroform, dried over Na2SO4, and distilled. The crude was vacuum distilled to give pure 70 (75 grams, 61.7%) as a light yellow syrup, Bp15 206-210° C. The structure was confirmed with NMR. IHNMR (CDCl3) δ 2.05 (s, 3H,O═C—CH3), 3.78(s, 3H,ester), 4.62(s, 2H,OCH2), 5.02 (s, 2H, CH2), 6.88 (d,2H,Ar), 7.33 (d, 2H,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-432821d5fb8e4b288e9b590e81a4d987
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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