Benzaldehyde → HCID 53819909, compound

HRID 2083500Notes

Reaction equation

HRID 2083500 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, compoundYield 89.9%

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 solution is stirred at room temperature and the product begins to separate from the solution as an oil after 30 minutes. The mixture is seeded with crystalline material and allowed to stand for about 16 hours at room temperature. The resulting slurry is poured onto 1.5 l. of ice-water, allowed to stand at room temperature for 2 hours, filtered and washed with cold water to yield 81.2 g of material, 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 the solution as an oil after 30 minutes
  2. additionThe resulting slurry is poured onto 1.5 l
  3. waitto stand at room temperature for 2 hours
  4. filtrationfiltered
  5. washwashed with cold water

Sources & evidence

ORD record
ord-2f539d9ef9124a44b3257449e373d03c
Source dataset
uspto-grants-1978_04
Patent number
US04085280

Reaction notes

Loading…