Triethylamine → 1-Methylheptyl 4-Benzyloxybenzoate

HRID 653998Notes

Reaction equation

HRID 653998 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.[CH3:18][CH:19]([OH:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].CN(C1C=CC=CN=1)C.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:26][CH:19]([CH3:18])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 200832-OctanolHCID 218852-DimethylaminopyridineHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 198881221-Methylheptyl 4-BenzyloxybenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-benzyloxybenzoic acid chloride (1.23 g) in methylene chloride (10 ml) was added slowly under ice cooling a solution of optically active 2-octanol (0.59 g), dimethylaminopyridine (0.55 g) and triethylamine (0.48 g) in methylene chloride (20 ml). The mixture was left to stand until it reached room temperature and was left to stand overnight in order to complete the reaction. The solution was poured in ice water and extracted with methylene chloride. The extracted layer was washed with dilute hydrochloric acid, water, 1N aqueous sodium carbonate solution and water, in this order, and dried over anhydrous magnesium sulfate. After the extract was distilled to remove the solvent until a crude product was obtained, the product was purified by toluene-silica gel column chromatography and further recrystallized from ethanol to obtain the titled compound (1.48 g).

Workup

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

Sources & evidence

ORD record
ord-a520c3f05b5e4f8d9fc557e6c64fb15a
Source dataset
uspto-grants-1992_07
Patent number
US05130050

Reaction notes

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