2-Methoxybenzaldehyde → HCID 54197120, compound

HRID 1076311Notes

Reaction equation

HRID 1076311 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[Cl:11][C:12]1[CH:35]=[CH:34][CH:33]=[CH:32][C:13]=1[CH:14]=[CH:15][CH2:16][C:17]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:23](=[O:25])[CH3:24])[CH2:18][CH2:19][C:20]([OH:22])=[O:21].[OH-].[Na+]>C(O)C.O>[Cl:11][C:12]1[CH:35]=[CH:34][CH:33]=[CH:32][C:13]=1[CH:14]=[CH:15][CH2:16][C:17]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:23](=[O:25])[CH:24]=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 14798Sodium HydroxideHCID 53835042HCID 53835042, compound

Product 1

HCID 54197120HCID 54197120, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

o-Methoxybenzaldehyde (2.72 g., 0.02 mole) in ethanol (10 ml.) is added to a solution of 4-(o-chlorocinnamyl)-4-phenyl-5-oxohexanoic acid (3.57 g., 0.01 mole) and sodium hydroxide (0.56 g., 0.014 mole) in water (50 ml.). The resulting mixture is heated on a steam bath for 24 hours. The reaction solution is cooled to room temperature, diluted with water (200 ml.), and extracted with ether to remove the excess o-methyoxybenzaldehyde. Ether is expelled from the aqueous phase by warming. The solution is cooled in an ice bath, acidified with dilute hydrochloric acid (10 ml.), and the yellow solid which precipitates is collected and air-dried. Several recrystallizations from ethanol yields a pale yellow material with m.p. 206.5°-209.5°C.

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. extractionextracted with ether
  3. customto remove the excess o-methyoxybenzaldehyde
  4. temperatureby warming
  5. temperatureThe solution is cooled in an ice bath
  6. customthe yellow solid which precipitates
  7. customis collected
  8. customair-dried
  9. customSeveral recrystallizations from ethanol
  10. customyields a pale yellow material with m.p. 206.5°-209.5°C.

Sources & evidence

ORD record
ord-5c7f5f7881ad45e284828eb2567ef3e5
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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