4-Fluorobenzaldehyde → HCID 54361987, compound

HRID 1720740Notes

Reaction equation

HRID 1720740 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:12].[O-]CC.[Na+]>C(O)C>[C:13]12([C:11](=[O:12])[CH:10]=[CH:6][C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 123126Methyl tricyclo(3.3.1.13,7)dec-1-yl ketoneHCID 2723922Sodium ethoxide

Product 1

HCID 54361987HCID 54361987, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 4-fluorobenzaldehyde (6.01 ml, 56.10 mmol, Aldrich) and 1-adamantyl methyl ketone (10.00 g, 56.10 mmol) in absolute ethanol (100 ml) was treated with a solution of sodium ethoxide in ethanol (21% by weight solution; 2.08 ml, 5.61 mmol). A precipitate soon fell out of solution. After stirring at room temperature for 48 hours, the mixture was cooled to -10° C. and the precipitate was collected by filtration. The solid was washed with cold ethanol, dried in vacuo and recrystallized from hexane. The title compound was obtained as an off-white solid (9.20 g, 57.8%).

Workup

  1. temperaturethe mixture was cooled to -10° C.
  2. filtrationthe precipitate was collected by filtration
  3. washThe solid was washed with cold ethanol
  4. customdried in vacuo
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-a0feab38f41c4e40baccd0c878ccec0f
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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