Benzyl Alcohol → HCID 178418417, compound

HRID 1635

Reaction equation

HRID 1635 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH2:16](O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 178418479HCID 178418479, compound

Product 1

HCID 178418417HCID 178418417, compound

Procedure

30 g of 6-hydroxynicotinic acid were treated with 500 ml of benzyl alcohol and 1 ml of concentrated sulfuric acid. After boiling at reflux for 3 days, the reaction mixture was poured on to ice-water, extracted several times with ethyl acetate, washed with water, dried over sodium sulfate and evaporated, firstly in a water-jet vacuum and then in a high vacuum. The semi-crystalline residue was filtered over silica gel (eluent hexane/ethyl acetate=2:1, then ethyl acetate) and recrystallized from ethyl acetate/hexane. There were obtained 19 g of benzyl 6-hydroxy-nicotinate in colourless crystals, m.p. 178°-179° C.

Workup

  1. temperatureat reflux for 3 days
  2. extractionextracted several times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated, firstly in a water-jet vacuum
  6. filtrationThe semi-crystalline residue was filtered over silica gel (eluent hexane/ethyl acetate=2:1
  7. customethyl acetate) and recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2e55407ae46c4beabc510d9038b027f8
Source dataset
uspto-grants-1998_03
Patent number
US05726191

Linked notes

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