Vanillin → Vanillin acetate

HRID 354827Notes

Reaction equation

HRID 354827 reaction equation
C(N(CC)CC)C.[O:8]=[CH:9][C:10]1[CH:18]=[CH:17][C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:19]([O:16][C:15]1[CH:17]=[CH:18][C:10]([CH:9]=[O:8])=[CH:11][C:12]=1[O:13][CH3:14])(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 1183VanillinHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 61229Vanillin acetateYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.8 liters, 20.1 moles) was added dropwise to a solution of vanillin (2.00 kg., 13.15 moles) and acetic anhydride (2.6 liters, 27.5 moles) in methylene chloride (11.3 liters) maintaining temperature below 25° C. After adding 4-dimethylaminopyridine (20 g.) the solution was stirred at room temperature for 30 minutes. The reaction mixture was washed twice with water, followed by 20% (w/w) hydrochloric acid and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to 8 liters. Hexane (15 liters) was added slowly while removing remaining methylene chloride. After cooling, 2.45 kg. (96% yield) product was filtered off. Recrystallization of a small sample from anhydrous ether gave the acetate as fine yellow needles, M.P. 76°-78° C.

Workup

  1. temperaturemaintaining temperature below 25° C
  2. washThe reaction mixture was washed twice with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo to 8 liters
  5. additionHexane (15 liters) was added slowly
  6. customwhile removing
  7. temperatureAfter cooling

Sources & evidence

ORD record
ord-f2dd43ebb90c4e5cbbd20d7ed3de13d4
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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