Hydrochloric Acid → 4-(4'-Chlorobenzyloxy)benzyl nicotinate

HRID 441707Notes

Reaction equation

HRID 441707 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1>C1C=CC=CC=1>[C:26]([O:13][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:7][CH2:6][C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 964394{4-[(4-Chlorobenzyl)oxy]phenyl}methanol

Product 1

HCID 1249984-(4'-Chlorobenzyloxy)benzyl nicotinate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 1.2g of 4-(4'-chlorobenzyloxy)benzyl alcohol, 1.0g of triethylamine and 25 ml of anhydrous benzene was added 0.9g of hydrochloride of nicotinoyl chloride at 10° C. The whole mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with water. The organic layer was dried over sodium sulfate and then concentrated in vacuo to give a crystalline residue. The residue was recrystallized from ethanol to give 1.2g of 4-(4'-chlorobenzyloxy)benzyl nicotinate, mp 101°-2° C.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a crystalline residue
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-166b093a59734e1b9bfa1c0c104a80b1
Source dataset
uspto-grants-1977_08
Patent number
US04042594

Reaction notes

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