3-Methyl-2-buten-1-OL → 3,3-dimethylpent-4-enoic aicd N,N-dimethylamide

HRID 1155561Notes

Reaction equation

HRID 1155561 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4]O.C[O:8][C:9](OC)([N:11]([CH3:13])[CH3:12])[CH3:10].CN(C)C(OC)=C>>[CH3:12][N:11]([CH3:13])[C:9](=[O:8])[CH2:10][C:2]([CH3:6])([CH3:1])[CH:3]=[CH2:4]

Participants

4

Reactant 3

HCID 111733-Methyl-2-buten-1-OLHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 132844661-Methoxy-N,N-dimethylethen-1-amine

Product 1

HCID 130201093,3-dimethylpent-4-enoic aicd N,N-dimethylamideYield 90%

Procedure

147 g of 3-methyl-but-2-en-1-ol are added to 180 g of a mixture of 72.5% by weight of N,N-dimethylacetamide-dimethylacetal and 27.5% by weight of 1-dimethylamino-1-methoxyethylene, and the batch is brought to 144° C. in the course of 80 minutes, whilst at the same time distilling the resulting methanol from the reaction mixture. The batch is then heated for 100 minutes at 144°-154° C. Distillation through a short column gives 205 g (90%) of 3,3-dimethyl-pent-4-enoic acid N,N-dimethylamide (of boiling point 70° C./2.6 mbar), corresponding to a yield of 90% of theory.

Workup

  1. customis brought to 144° C. in the course of 80 minutes, whilst at the same time
  2. distillationdistilling the resulting methanol from the reaction mixture
  3. temperatureThe batch is then heated for 100 minutes at 144°-154° C
  4. distillationDistillation through a short column

Sources & evidence

ORD record
ord-191ac78c87774c488cafc55130be801d
Source dataset
uspto-grants-1981_11
Patent number
US04302584

Reaction notes

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