Sodium Acetate → HCID 66890465, compound

HRID 253267Notes

Reaction equation

HRID 253267 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[C:14]([O-])(=[O:16])[CH3:15].[Na+]>C(OC(=O)C)(=O)C>[C:14]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 66890465HCID 66890465, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Methyl 3-hydroxy-4-(methyloxy)benzoate (27 g, 149 mmol.) was taken into acetic anhydride (150 mL) followed by addition of sodium acetate (24 g, 298 mmol.) and the resulting mixture was stirred at room temperature over 20 hours. The solid was filtered and washed once with ethyl acetate and the combined organic layers concentrated in vacuo to a slurry. The solid was collected by filtration, washed once with water and dried in vacuo to provide methyl 3-(acetyloxy)-4-(methyloxy)benzoate (25.9 g, 77% yield) as a white solid. 1H NMR (400 MHz, CDCl3): 7.92 (dd, 1H), 7.70 (d, 1H), 6.97 (d, 1H), 3.88 (s, 3H), 3.87 (s, 3H), 2.32 (s, 3H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed once with ethyl acetate
  3. concentrationthe combined organic layers concentrated in vacuo to a slurry
  4. filtrationThe solid was collected by filtration
  5. washwashed once with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3a63ff80cef147999d6e69cf8fee3d8a
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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