Vanillin → Vanillin acetate

HRID 1898758Notes

Reaction equation

HRID 1898758 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.C(Cl)Cl.CCOCC>[C:19]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])(=[O:21])[CH3:20]

Participants

7

Reactant 3

HCID 1183VanillinHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 61229Vanillin acetate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of vanillin (60.8 g), triethylamine (60 ml), acetic anhydride (44 ml), and 4-dimethylaminopyridine (1.0 g) in methylene chloride (800 ml) is stirred at room temperature for about 30 minues, and the volume then reduced by 50% in vacuo. The residue is diluted with ether and the solution washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product.

Workup

  1. washthe solution washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-120dc1751cde4571b1c1a8542de45155
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

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