Benzaldehyde → HCID 53819909, compound

HRID 1111722Notes

Reaction equation

HRID 1111722 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][C:9](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 955922-Phenylcyclohexanone

Product 1

HCID 53819909HCID 53819909, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 60.0 g of 2-phenylcyclohexanone in 400 ml of ethanol is stirred and treated with 160 ml of 15% aqueous sodium hydroxide and 53.0 g of benzaldehyde. The resulting solution is stirred at room temperature and the product begins to separate from solution as an oil after 30 minutes. The mixture is seeded with crystalline material and allowed to stand overnight at room temperature. The resulting slurry is poured onto 1.5 liters of ice-water, allowed to stand at room temperature for 2 hours, filtered and washed with cold water. This material weights 81.2 g, melting point 75°-78° C. After crystallization from 200 ml of isopropanol, the product weighs 62.1 g; melting point 85°-87° C. A small sample, recrystallized from ethanol, melts at 86°-88° C.

Workup

  1. customto separate from solution as an oil after 30 minutes
  2. additionThe resulting slurry is poured onto 1.5 liters of ice-water
  3. waitto stand at room temperature for 2 hours
  4. filtrationfiltered
  5. washwashed with cold water
  6. customAfter crystallization from 200 ml of isopropanol
  7. customA small sample, recrystallized from ethanol, melts at 86°-88° C.

Sources & evidence

ORD record
ord-75703dc566e74a21813a5d5eb54cf3e4
Source dataset
uspto-grants-1978_10
Patent number
US04118558

Reaction notes

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