Triethylamine → Propanoic acid, 2,2-dimethyl-, (((4-((4-chlorophenyl)methyl)phenoxy)acetyl)oxy)methyl ester

HRID 262322Notes

Reaction equation

HRID 262322 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27]([O:33][CH2:34]Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O>[C:27]([O:33][CH2:34][O:14][C:13](=[O:15])[CH2:12][O:11][C:10]1[CH:16]=[CH:17][C:7]([CH2:6][C:5]2[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 42121Acetic acid, 2-(4-(4-chlorobenzyl)phenoxy)-HCID 87885Chloromethyl pivalate

Product 1

HCID 3044347Propanoic acid, 2,2-dimethyl-, (((4-((4-chlorophenyl)methyl)phenoxy)acetyl)oxy)methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.3 g (0.06 mol) of 4-(4'-chlorobenzyl)-phenoxy acetic acid in 50 ml of dimethylformamide are added 6.0 g (0.06 mol) of triethylamine, whereafter the mixture is stirred for 30 minutes at room temperature and, after adding 9.0 (0.06 mol) of chloromethyl pivalate, is heated for 6 hours in an oil bath at 85°-90° C. The residue which is obtained by concentration by evaporation at reduced pressure in a Buchi rotary evaporator is washed with water and extracted with ether. The ethereal solution is once again washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation in the Buchi rotary evaporator, an oil being obtained which quickly solidifies. By recrystallisation from ether/n-hexane, 9.5 g of product are obtained in the form of white crystals with the melting point 54°-55° C.

Workup

  1. temperatureis heated for 6 hours in an oil bath at 85°-90° C
  2. customThe residue which is obtained by concentration by evaporation at reduced pressure in a Buchi rotary evaporator
  3. washis washed with water
  4. extractionextracted with ether
  5. washThe ethereal solution is once again washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationconcentrated by evaporation in the Buchi rotary evaporator
  8. customan oil being obtained which
  9. customBy recrystallisation from ether/n-hexane, 9.5 g of product
  10. customare obtained in the form of white crystals with the melting point 54°-55° C.

Sources & evidence

ORD record
ord-5fe2a03e8f7d496a9a9961c402d9b5b9
Source dataset
uspto-grants-1979_05
Patent number
US04153803

Reaction notes

Loading…