Dichloromethane → N,N-Diethyl-2-(3,5-di-tert-butyl-4-hydroxyphenyl)acetamide

HRID 1379313Notes

Reaction equation

HRID 1379313 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]([OH:19])=O)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].ClCCl.S(Cl)(Cl)=O.[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28]>CCCCCCC.CN(C)C=O>[CH2:27]([N:29]([CH2:30][CH3:31])[C:17](=[O:19])[CH2:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=1)[CH3:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 27751103,5-Bis(1,1-dimethylethyl)-4-hydroxybenzeneacetic acid

Product 1

HCID 18924148N,N-Diethyl-2-(3,5-di-tert-butyl-4-hydroxyphenyl)acetamideYield 67.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8900HeptaneSolvent2×

Procedure

7.92 g (0.03 Mol) of (3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid are stirred overnight in 40 ml of heptane and 20 ml of dichloromethane with 4 ml of thionyl chloride and 4 drops of N,N-dimethylformamide. An additional 90 ml of heptane are added and then 90 ml of solvent and the excess amount of thionyl chloride are distilled off. The residual solution is cooled to room temperature and then 7.5 ml (0.072 mol) of diethylamine are added dropwise. The mixture is stirred one hour, then washed with water, 5% hydrochloric acid and water again. The solvent is evaporated in vacuo, and the residue is crystallized twice from acetonitrile to give 6.5 g of the intermediate product as colorless needles, melting at 111°-113° C.

Workup

  1. distillation90 ml of solvent and the excess amount of thionyl chloride are distilled off
  2. washwashed with water, 5% hydrochloric acid and water again
  3. customThe solvent is evaporated in vacuo
  4. customthe residue is crystallized twice from acetonitrile

Sources & evidence

ORD record
ord-3695ad6018504a4d8c6a5031af1d57c1
Source dataset
uspto-grants-1997_09
Patent number
US05670692

Reaction notes

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