Hydrochloric Acid → HCID 19930299, compound

HRID 22432Notes

Reaction equation

HRID 22432 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[C:31](C#N)=[CH:30][CH:29]=[CH:28][C:27]=2C#N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:36][OH:37].Cl.[CH3:39][OH:40].O>C1(C)C=CC=CC=1>[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[C:27]([CH:36]=[O:37])=[CH:28][CH:29]=[CH:30][C:31]=2[CH:39]=[O:40])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19930263HCID 19930263, compoundHCID 21225700DiisobutylaluminumhydrideHCID 22242641Methanol--water (1/1)

Product 1

HCID 19930299HCID 19930299, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of diisobutylaluminium hydride in toluene (3.1 ml, 4.6 mmol) was added dropwise to a stirred solution of 2-(9-phenylnonyl)-1,3-benzenedicarbonitrile (0.70 g, 2.1 mmol) in dry toluene (30 ml) under nitrogen, cooled in an ice bath. After one hour at room temperature methanol (1 ml) was added cautiously, followed by methanol:water (1:1, 1 ml) and 5M hydrochloric acid (15 ml). The mixture was extracted with diethyl ether (20 ml) and the extracts dried, filtered and evaporated to a yellow oil (0.8 g). Chromatography on flash silica eluting with dichloromethane gave 2-(9-phenylnonyl)-1,3benzenedicarboxaldehyde as a colourless oil.

Workup

  1. temperaturecooled in an ice bath
  2. extractionThe mixture was extracted with diethyl ether (20 ml)
  3. customthe extracts dried
  4. filtrationfiltered
  5. customevaporated to a yellow oil (0.8 g)

Sources & evidence

ORD record
ord-d59791741d034daf91ff6fbb2d4f823d
Source dataset
uspto-grants-1995_06
Patent number
US05428065

Reaction notes

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