Acetic Anhydride → 3,4,5-Trimethoxyphenyl acetate

HRID 1095266Notes

Reaction equation

HRID 1095266 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 695053,4,5-Trimethoxyphenol

Product 1

HCID 2762803,4,5-Trimethoxyphenyl acetateYield 93%

Procedure

A solution of 3,4,5-trimethoxyphenol (5.52 g, 30 mmol) in acetic anhydride (15 mL) was refluxed for 4 h. The reaction mixture was poured onto crushed ice (50 g). The resulting precipitate was collected and washed with water. The residue was dried in vacuum at 50° C. for 24 h to afford white crystals (6.31 g, 93%), 74-75° C.; 1H NMR (CDCl3, 200 M Hz) δ 6.34 (s, 2H), 3.83 (s, 6H), 3.82 (s, 3H), 2.29 (s, 3H); 13C NMR (CDCl3, 50 M Hz) δ 169.6 (s), 153.5 (s, 2C), 146.7 (s), 135.8 (s), 99.1 (d, 2C), 60.9 (q), 56.1 (q, 2C), 21.1 (q).

Workup

  1. additionThe reaction mixture was poured
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customThe residue was dried in vacuum at 50° C. for 24 h

Sources & evidence

ORD record
ord-ca35b1a90ca14b7d9c7db00dbb8cc48a
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

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