Acetic Anhydride → 4-Tert-butylcinnamic acid

HRID 1017144Notes

Reaction equation

HRID 1017144 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14].C([O-])(=O)C.[Na+]>O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:14][C:13]([OH:16])=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 703244-tert-ButylbenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 7248384-Tert-butylcinnamic acidYield 134.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3 L one neck flask fit with a reflux condenser, magnetic stirrer, and nitrogen inlet was charged with p-t-butylbenzaldehyde (145.5 g, 0.90 mol), acetic anhydride (106 mL, 1.12 mol), and sodium acetate (7.36 g, 0.90 mol). After refluxing for 48.5 hours the reaction was cooled and water was added slowly to roughly triple the total volume as a yellow solid formed. The solids were filtered and washed with water (200 mL), reslurried in water and refiltered and washed again with water (750 mL total). The product was partially dried in the vacuum oven to give 4-t-butlycinnamic acid (248 g). 1HNMR (CD3SOCD3, 500 MHz) mostly trans isomer δ7.58 (d, JAB=8.5 Hz, 2H); 7.54 (d, J=15.5 Hz, 1H); 7.41 (d, JAB=7.5 Hz, 2H); 6.46 (d, J=16.0 Hz, 1H); 1.26 (s, 9H).

Workup

  1. temperatureAfter refluxing for 48.5 hours the reaction
  2. temperaturewas cooled
  3. customformed
  4. filtrationThe solids were filtered
  5. washwashed with water (200 mL)
  6. washwashed again with water (750 mL total)
  7. customThe product was partially dried in the vacuum oven

Sources & evidence

ORD record
ord-364fbb7c20084232b759bbcc886b582a
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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