Pyridine → 3-(Acetyloxy)-2,2-dimethylpropanoic acid

HRID 978433Notes

Reaction equation

HRID 978433 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:11][C:12]([CH3:18])([CH2:16][OH:17])[C:13]([OH:15])=[O:14]>CN(C1C=CN=CC=1)C.CCOCC>[C:1]([O:17][CH2:16][C:12]([CH3:18])([CH3:11])[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 785483-Hydroxy-2,2-dimethylpropionic acid

Product 1

HCID 131926213-(Acetyloxy)-2,2-dimethylpropanoic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

Acetyl chloride (4.52 g, 58.2 mmol) was added dropwise to a cold (0° C.) pyridine solution (10 ml) of 2,2-dimethyl-3-hydroxypropionic acid (5.5 g, 46.5 mmol) and 4-DMAP (0.57 g, 4.65 mmol). After stirring overnight at ambient temperature, the reaction was poured into ether (200 ml). This mixture was washed with 10% HCl (2×20 ml), and saturated brine (2×25 ml) and the resulting ethereal solution was dried (MgSO4). Evaporation gave the title compound as a pale yellow solid which was used in the next step without further purification. NMR (CDCl3) δ4.13 (2H, s), 2.08 (3H, s), 1.26 (6H, s).

Workup

  1. washThis mixture was washed with 10% HCl (2×20 ml), and saturated brine (2×25 ml)
  2. dry with materialthe resulting ethereal solution was dried (MgSO4)
  3. customEvaporation

Sources & evidence

ORD record
ord-9c3ec567e7864c2ca820da3e4f0276cd
Source dataset
uspto-grants-1987_05
Patent number
US04665091

Reaction notes

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