Hydrochloric Acid → ALPHA-CYANOCINNAMIC ACID

HRID 1615917Notes

Reaction equation

HRID 1615917 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1.Cl>N1C=CC=CC=1>[C:5]([C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1/[CH:1]=[CH:12]/[C:13]([OH:15])=[O:14])#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 1012092-Cyanobenzaldehyde

Product 1

HCID 785072ALPHA-CYANOCINNAMIC ACIDYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-formylbenzonitrile (4.17 g, 31.8 mmol), malonic acid (7.61 g, 73.1 mmol), and piperidine (0.314 mL, 3.18 mmol) in pyridine (40 mL) was heated to reflux for 2 hr. The solution was cooled and poured into crushed ice (150 mL) and 12N HCl (30 mL). The white precipitate was filtered, washed with water, and air dried to give a tan powder (3.85 g, 70%). 1H NMR (500 MHz, DMSO-d6) δ 12.81 (br. s., 1H), 8.09 (d, J=7.9 Hz, 1H), 7.93 (dd, J=7.8, 0.9 Hz, 1H), 7.80-7.74 (m, 2H), 7.62 (td, J=7.6, 0.9 Hz, 1H), 6.80 (d, J=15.9 Hz, 1H).

Workup

  1. temperatureto reflux for 2 hr
  2. temperatureThe solution was cooled
  3. additionpoured
  4. filtrationThe white precipitate was filtered
  5. washwashed with water, and air
  6. customdried

Sources & evidence

ORD record
ord-1e0842034a0444edaaaa099facb0ad99
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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