Benzyl Alcohol → HCID 21107062, compound

HRID 1765319Notes

Reaction equation

HRID 1765319 reaction equation
[N:1]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:14])[CH2:5]1)=[C:2]=[O:3].[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>C1C=CC=CC=1>[CH2:15]([O:22][C:2]([NH:1][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:14])[CH2:5]1)=[O:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 21107064HCID 21107064, compound

Product 1

HCID 21107062HCID 21107062, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 3-isocyanato-1-oxo-1,2,3,4-tetrahydronaphthalene (10 g), benzyl alcohol (7.3 g), dry pyridine (3 mL), and benzene (50 mL) was refluxed for 90 min. At the conclusion of this period, the solution was cooled to room temperature, diluted with benzene (150 mL), and then washed with 5% aqueous hydrochloric acid solution (60 mL twice). The organic layer was dried and evaporated under vacuum to yield a residue. The residue was crystallized by dissolving in benzene (35 mL) and diluting with petroleum ether (25 mL). Crystals thus obtained were recrystallized in the same manner to obtain the title compound (6.6 g, mp 79.5–81.5° C.).

Workup

  1. washwashed with 5% aqueous hydrochloric acid solution (60 mL twice)
  2. customThe organic layer was dried
  3. customevaporated under vacuum
  4. customto yield a residue
  5. customThe residue was crystallized
  6. dissolutionby dissolving in benzene (35 mL)
  7. additiondiluting with petroleum ether (25 mL)
  8. customCrystals thus obtained
  9. customwere recrystallized in the same manner

Sources & evidence

ORD record
ord-9391ddc514104731a9cb2994a2994cfb
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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