N,N-Dimethylbenzylamine → 3-Ethoxy-4-hydroxybenzaldehyde;2-methylpropanoic acid

HRID 363287Notes

Reaction equation

HRID 363287 reaction equation
[O:1]=[CH:2][C:3]1[CH:12]=[CH:11][C:9]([OH:10])=[C:5]([O:6][CH2:7][CH3:8])[CH:4]=1.CN(CC1C=CC=CC=1)C.C[O:24]C(C)(C)C.C(Cl)(=O)C(C)C>O>[C:2]([OH:24])(=[O:1])[CH:3]([CH3:12])[CH3:4].[O:1]=[CH:2][C:3]1[CH:12]=[CH:11][C:9]([OH:10])=[C:5]([O:6][CH2:7][CH3:8])[CH:4]=1

Participants

6

Reactant 4

HCID 7681N,N-DimethylbenzylamineHCID 8467EthylvanillinHCID 15413tert-Butyl methyl etherHCID 62325Isobutyryl chloride

Product 1

HCID 573576583-Ethoxy-4-hydroxybenzaldehyde;2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

166 g (1 mol) of ethylvanillin and 160 g (1.33 mol) of N,N-dimethylbenzylamine are introduced into 800 ml of tert-butyl methyl ether in a stirred apparatus with the exclusion of moisture. 128 g (1.2 mol) of isobutyroyl chloride are added over the course of 1.5 h, during which the reaction temperature rises to about 38° C. The reaction mixture is stirred overnight at room temperature and then poured into about 1 l of water. The organic phase is separated off, washed with hydrochloric acid, 5% sodium hydroxide solution and water, dried and evaporated, giving a residue of 238 g of crude ethylvanillin isobutyrate, which is recrystallized from 240 ml of isopropanol. Yield 215 g of ethylvanillin isobutyrate; m.p. 57° C.

Workup

  1. customrises to about 38° C
  2. customThe organic phase is separated off
  3. washwashed with hydrochloric acid, 5% sodium hydroxide solution and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-7d1e04d453b34b3fbdefd0b380633b16
Source dataset
uspto-grants-1999_02
Patent number
US05874398

Reaction notes

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