Salicylaldehyde → alpha-(2'-Hydroxybenzylidene)-delta-valerolactone

HRID 2085230Notes

Reaction equation

HRID 2085230 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:10]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C1(C)C=CC=CC=1>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[C:11]1[CH2:12][CH2:13][CH2:14][O:15][C:10]1=[O:16]

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 10953Delta-Valerolactone

Product 1

HCID 69704382alpha-(2'-Hydroxybenzylidene)-delta-valerolactoneYield 27.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Salicylaldehyde (15.2 g) and δ-valerolactone (25 g) were dissolved in toluene (150 ml). By the reaction in the same manner as in Example 307, oily α-(2′-hydroxybenzylidene)-δ-valerolactone (7.0 g) was obtained. Dimethylformamide (70 ml) and potassium carbonate (9.5 g) were added hereto and (S) -glycidyl nosylate (8.9 g) was added. The mixture was stirred at 40° C. for 2 hr. The reaction mixture was concentrated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the oily title compound (7.8 g). The reaction in the same manner as in Example 307 using this product (1.0 g) and 4-(naphthalen-2-yl)piperidine (1.0 g) in methanol (50 ml) was performed and the obtained oil was recrystallized from ethyl acetate to give the title compound (0.38 g), melting point 142-144° C.

Workup

  1. customBy the reaction in the same manner as in Example 307

Sources & evidence

ORD record
ord-7f35f8d2bbe74c748a47e2ed8866d6c6
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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