Benzaldehyde → Benzylidene Dihexanoate

HRID 1276545

Reaction equation

HRID 1276545 reaction equation
[CH:1](=[O:8])[C:2]1C=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(=O)(=O)(O)O.[C:29](Cl)(Cl)(Cl)Cl>>[C:9]([O:16][CH:17]([O:23][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:18]1[CH:29]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 5943Carbon TetrachlorideHCID 74918Hexanoic anhydride

Product 1

HCID 22116394Benzylidene Dihexanoate

Procedure

Benzaldehyde (26.3 g, 0.25 mol) and hexanoic acid anhydride (53.3 g, 0.25 mol) were dissolved in carbontetrachloride (200 ml) under N2 -atrnosphere. Catalytic amounts of sulfuric acid was added and the reaction mixture stirred at room temperature for 1 hr. The reaction mixture was evaporated over night, the residue dissolved in hexane and the solution filtered through a bed of silica. The filtrate was purified on a silica column, eluting with hexane. The evaporated eluate was a colourless oil and the yield was 14.0 g, 18% of the theoretical. 1H- and 13C NMR (CDCl3) d (ppm) rel. to TMS: 7.72 (s, 1H, CH(OC5H11)2), 7.58-7.39 (m, 5H, Ar-H), 2.37 (double t, 4 H, COCH2), 1.64 (m, 4H, COCH2CH2), 1.30 (m, 4H,CH2CH2CH3) and 0.88 (t, 6H, CH3); 171.524 (C=O), 135.688, 129.523, 128.466 and 126.547 (Ar), 89.398 (CH(OC5H11)2), 33.965, 31.030, 24.235 and 22.179 (CH2) and 13.777 (CH3).

Workup

  1. customThe reaction mixture was evaporated over night
  2. dissolutionthe residue dissolved in hexane
  3. filtrationthe solution filtered through a bed of silica
  4. customThe filtrate was purified on a silica column
  5. washeluting with hexane

Sources & evidence

ORD record
ord-0ac83dd932234a3e9b8cd9b5398f47aa
Source dataset
uspto-grants-2000_12
Patent number
US06166074

Linked notes

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