Dicyclohexylcarbodiimide → (+)-4-[3-{2(S)-methylbutoxy}propyl]phenyl 4-decyloxybenzoate

HRID 1770062

Reaction equation

HRID 1770062 reaction equation
[CH3:1][C@@H:2]([CH2:15][CH3:16])[CH2:3][O:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[CH2:17]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>>[CH2:17]([O:27][C:28]1[CH:29]=[CH:30][C:31]([C:32]([O:14][C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][CH2:5][O:4][CH2:3][C@@H:2]([CH3:1])[CH2:15][CH3:16])=[CH:13][CH:12]=2)=[O:33])=[CH:35][CH:36]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 1385274-(Decyloxy)benzoic acidHCID 22844682(+)-4-[3-{2(S)-methylbutoxy}propyl]phenol

Product 1

HCID 22844683(+)-4-[3-{2(S)-methylbutoxy}propyl]phenyl 4-decyloxybenzoateYield 90.4%

Procedure

Into a four-necked flask equipped with a stirrer and a thermometer were charged 1.11 g (5 millimole) of (+)-4-[3-{2(S)-methylbutoxy}propyl]phenol, 1.67 g (6 millimole) of 4-decyloxybenzoic acid and 30 ml of anhydrous dichlomethane, and then 1.22 g (6 millimole) of N,N'-dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine were added thereto, followed by stirring at room temperature for one day. After completion of the reaction, precipitates formed were filtered off and diluted with 200 ml of toluene. The organic phase was washed with water, 5% aqueous acetic acid solution, water, 5% aqueus sodium hydrogen carbonate solution and water in this order and then dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by silica gel column chromttography (eluent: toluene-ethyl acetate) to obtain 2.18 g (yield: 90.4%) of (+)-4-[3-{2(S)-methylbutoxy}propyl]phenyl 4-decyloxybenzoate.

Workup

  1. customInto a four-necked flask equipped with a stirrer
  2. customAfter completion of the reaction
  3. customprecipitates
  4. customformed
  5. filtrationwere filtered off
  6. additiondiluted with 200 ml of toluene
  7. washThe organic phase was washed with water, 5% aqueous acetic acid solution, water, 5% aqueus sodium hydrogen carbonate solution and water in this order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromttography (eluent: toluene-ethyl acetate)

Sources & evidence

ORD record
ord-b3b5a101e514463a82fb6d1fda8d861a
Source dataset
uspto-grants-1995_01
Patent number
US05385693

Linked notes

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