Benzyl Alcohol → 9-(Benzyloxy)-9-oxononanoic acid

HRID 580803Notes

Reaction equation

HRID 580803 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[C:13]([OH:25])(=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].C(O)C1C=CC=CC=1>C1C=CC=CC=1>[C:13]([O:25][CH2:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 2266Azelaic AcidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 142502649-(Benzyloxy)-9-oxononanoic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Toluene-4-sulfonic acid monohydrate (0.71 g, 3.72 mmol) is added to a suspension of azelaic acid (25.0 g, 132.82 mmol) in benzene (550 ml). The mixture is heated to 80° C., whereafter benzyl alcohol (14.36 g, 132.82 mmol) in benzene (50 ml) is added dropwise to the resulting solution. The reaction mixture is refluxed overnight and water is removed azeotropically with a Dean Stark trap. The reaction mixture is allowed to cool, the white precipitate which forms is removed by filtration and the filtrate is concentrated to a brownish oil under reduced pressure. The crude product (33.97 g) is dissolved in dichloromethane (50 ml) and purified by flash chromatography, on a 5.5×15 cm silica column with dichloromethane/methanol (20:1) as eluant. The product, a yellow oil, is dried under vacuum. The oil crystallizes after a few hours at room temperature. Yield: 12.8 g (35%). 13C NMR (75 MHz, CDCl3): δ 24.5, 24.8, 28.8, 34.0, 34.2, 66.1, 128.2, 128.5, 136.1, 173.6, 180.0.

Workup

  1. additionis added dropwise to the resulting solution
  2. temperatureThe reaction mixture is refluxed overnight
  3. customwater is removed azeotropically with a Dean Stark trap
  4. temperatureto cool
  5. customthe white precipitate which forms is removed by filtration
  6. concentrationthe filtrate is concentrated to a brownish oil under reduced pressure
  7. dissolutionThe crude product (33.97 g) is dissolved in dichloromethane (50 ml)
  8. custompurified by flash chromatography, on a 5.5×15 cm silica column with dichloromethane/methanol (20:1) as eluant
  9. customThe product, a yellow oil, is dried under vacuum
  10. customThe oil crystallizes after a few hours at room temperature

Sources & evidence

ORD record
ord-22d59e6e166d46e28468a3e66e3031a1
Source dataset
uspto-grants-1999_07
Patent number
US05919753

Reaction notes

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