N,N-Dimethylaniline → Butanoic acid, 4-chloro-, 1,1-dimethylethyl ester

HRID 130596Notes

Reaction equation

HRID 130596 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].CN(C)C1C=CC=CC=1.[C:17]([OH:21])([CH3:20])([CH3:19])[CH3:18]>C(OCC)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:6]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6386tert-ButanolHCID 783704-Chlorobutyryl chloride

Product 1

HCID 527695Butanoic acid, 4-chloro-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 4-chlorobutyryl chloride (93 g, 0.66 mol), N,N-dimethylaniline (80 g, 0.66 mol) and tert-butanol (0.66 mol) in ethyl ether (100 mL) was refluxed for 5 h. The reaction was cooled, diluted with ether and washed with water, 10% citric acid, saturated NaCl and dried over Na2SO4. Crude product obtained after evaporation of the solvent was distilled under vacuum (10 mmHg). Pure product (79 g, 67%) boiling at 57-58° C. was collected. 1H NMR (DMSO-d6) δ 3.64 (t, J=7 Hz, 2H), 2.35 (t, J=7 Hz, 2H), 1.93 (q, 2H), 1.41 (s, 9H).

Workup

  1. temperaturewas refluxed for 5 h
  2. temperatureThe reaction was cooled
  3. washwashed with water, 10% citric acid, saturated NaCl
  4. dry with materialdried over Na2SO4
  5. customCrude product obtained
  6. customafter evaporation of the solvent
  7. distillationwas distilled under vacuum (10 mmHg)
  8. customPure product (79 g, 67%) boiling at 57-58° C. was collected

Sources & evidence

ORD record
ord-1faaece79fc84df0b19a0daa1dfc88fb
Source dataset
uspto-grants-2008_06
Patent number
US07381818B2

Reaction notes

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