Pivaloyl chloride → 2,2-Dimethyl-propionic acid 10-bromodecyl ester

HRID 339149

Reaction equation

HRID 339149 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[CH3:13][C:14]([CH3:19])([CH3:18])[C:15](Cl)=[O:16]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:15](=[O:16])[C:14]([CH3:19])([CH3:18])[CH3:13]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 1045071-Decanol, 10-bromo-

Product 1

HCID 573337812,2-Dimethyl-propionic acid 10-bromodecyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

2,2-dimethyl-propionic acid 10-bromodecyl ester was prepared in 85% yield by treatment of 10-bromodecan-1-ol with trimethylacetyl chloride in the presence of pyridine and 4-dimethylaminopyridine at room temperature in dithlcromethane. After 18 hrs, the reaction was quenched by the addition of dilute hydrochloric acid worked up and filtered through silica to provide 2,2-dimethyl-propionic acid 10-bromodecyl ester.

Workup

  1. customthe reaction was quenched by the addition of dilute hydrochloric acid
  2. filtrationfiltered through silica
  3. customto provide 2,2-dimethyl-propionic acid 10-bromodecyl ester

Sources & evidence

ORD record
ord-628f7a29ee99450882d8c5c0698fc2e3
Source dataset
uspto-grants-2014_11
Patent number
US08889894B2

Linked notes

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