Benzyl Alcohol → HCID 13255306, compound

HRID 903977Notes

Reaction equation

HRID 903977 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:18])[C:5]2[C:10]([C:11](=[O:15])[C:12]=1[O:13][CH3:14])=[C:9]([C:16]#[N:17])[CH:8]=[CH:7][CH:6]=2.C(O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:1]([O:2][C:3]1[C:4](=[O:18])[C:5]2[C:10]([C:11](=[O:15])[C:12]=1[O:13][CH2:14][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[C:9]([C:16]#[N:17])[CH:8]=[CH:7][CH:6]=2)[C:3]1[CH:4]=[CH:5][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 132552666,7-Dimethoxy-5,8-dioxo-5,8-dihydronaphthalene-1-carbonitrile

Product 1

HCID 13255306HCID 13255306, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14b From Example 9 (972 mg, 4 mmol) is dissolved in tetrahydrofuran (100 ml) containing benzyl alcohol (8 ml) and the tetrahydrofuran (40 ml) is distilled off. The remaining solution is cooled to 15° and sodium hydride (5 mg) with 3 A molecular sieve (2 g) is added. The resulting mixture is stirred at 15°-20° for 20 minutes. The mixture is filtered through a celite bed, the filtrate concentrated to dryness and the residue crystallized from isopropanol giving 1.01 g (64%) of 23 with mp 118°-121°.

Workup

  1. distillationthe tetrahydrofuran (40 ml) is distilled off
  2. temperatureThe remaining solution is cooled to 15°
  3. additionsodium hydride (5 mg) with 3 A molecular sieve (2 g) is added
  4. filtrationThe mixture is filtered through a celite bed
  5. concentrationthe filtrate concentrated to dryness
  6. customthe residue crystallized from isopropanol giving 1.01 g (64%) of 23 with mp 118°-121°

Sources & evidence

ORD record
ord-353a5ea894b54e4b8827b3378485dcf5
Source dataset
uspto-grants-1980_10
Patent number
US04229478

Reaction notes

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