Water → 3-(4'-Butoxybenzylidene)-bornan-2-one

HRID 1578059Notes

Reaction equation

HRID 1578059 reaction equation
[C:1]12([CH3:11])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].C[O-].[Na+].[CH2:15]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH2:16][CH2:17][CH3:18].O>C1(C)C=CC=CC=1>[CH2:15]([O:19][C:20]1[CH:21]=[CH:22][C:23]([CH:24]=[C:4]2[CH:5]3[C:8]([CH3:10])([CH3:9])[C:1]([CH3:11])([CH2:7][CH2:6]3)[C:2]2=[O:3])=[CH:26][CH:27]=1)[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 2537CamphorHCID 798134-ButoxybenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 540235863-(4'-Butoxybenzylidene)-bornan-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 100 millimols (15.2 g) of camphor in 250 ml of toluene is heated for 1 hour at the boil with 100 mmols (5.4 g) of sodium methylate. After cooling, 100 mmols (17.8 g) of p-butoxybenzaldehyde are introduced and the mixture is heated at the reflux temperature for 4 hours. The reaction mixture is cooled and 50 ml of water are then added; the toluene phase is separated off, washed with water, dried over sodium sulphate and concentrated to dryness. The solid residue is crystallised from aqueous isopropanol. After drying, 12 g of a white powder, which melts at 62°, are collected.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture is heated at the reflux temperature for 4 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe toluene phase is separated off
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness
  8. customThe solid residue is crystallised from aqueous isopropanol
  9. customAfter drying
  10. custom12 g of a white powder, which melts at 62°, are collected

Sources & evidence

ORD record
ord-382c3a0e1c58473397c3af31952ef314
Source dataset
uspto-grants-1981_09
Patent number
US04290974

Reaction notes

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