Chloride → Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)nonyl ester

HRID 247782

Reaction equation

HRID 247782 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:31])([F:30])[CH:20]([OH:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].CN(C1C=CC=CN=1)C.[Cl-]>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:29][CH:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:19]([F:18])([F:30])[F:31])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 218852-DimethylaminopyridineHCID 37664104-BenzyloxybenzoylchlorideHCID 38644641,1,1-Trifluorodecan-2-ol

Product 1

HCID 14745753Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)nonyl esterYield 96.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-benzyloxybenzoic acid chloride (1.23 g) in methylene chloride (10 ml) was slowly added under ice cooling a solution of optically active 1,1,1-trifluoro-2-decanol (0.96 g), dimethylaminopyridine (0.55 g) and triethylamine (0.48 g) in methylane chloride (20 ml). The mixture was left to stand until it reached room temperature and allowed to react overnight. The mixture was poured in ice water and extracted with methylene chloride. The extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water in this order, and was dried over anhydrous magnesium sulfate. After the solution was distilled to remove the solvent, the crude product thus obtained was purified by toluene-silica-gel column chromatography and recrystallized from ethanol to obtain the titled compound (1.84 g).

Workup

  1. waitThe mixture was left
  2. customreached room temperature
  3. customto react overnight
  4. extractionextracted with methylene chloride
  5. washThe extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water in this order
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationAfter the solution was distilled
  8. customto remove the solvent
  9. customthe crude product thus obtained
  10. customwas purified by toluene-silica-gel column chromatography
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-859e072770fa41648e889dcb531ae8cb
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

Loading…