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

HRID 1771049Notes

Reaction equation

HRID 1771049 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 2266Azelaic Acid

Product 1

HCID 142502649-(Benzyloxy)-9-oxononanoic acidYield 47%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A stirred mixture of nonanedioic acid (18.8 g; 0.10 mol), benzyl alcohol (10.8 g; 0.10 mol), and p-toluenesulphonic acid (0.2 g) in toluene (200 mL) was refluxed through a Dean-Stark trap overnight. The mixture was cooled to ambient temperature and extracted with 10% aqueous N-methyl-D-glucamine (4×25 mL). The last extract was a milky emulsion. The first three extracts were combined, acidified with 1 M HCl (50 mL), and filtered to give recovered nonanedioic acid (3.8 g). The emulsion was acidified with 1 M HCl and allowed to separate overnight. The organic layer was evaporated and the residue dissolved in hexane (200 mL) and diethyl ether (50 mL). The solution was extracted with 10% N-methyl-D-glucamine (2×50 mL) (emulsions broken by adding a little ethanol). The organic solution was washed with water (1×25 mL) and the combined aqueous solution was acidified with 1 M HCl (150 mL). After extraction with dichloromethane-tetrahydrofuran (4:1) (5×10 mL), the combined extracts were dried (Na2SO4), filtered, and evaporated. 13.0 g (47%) product was obtained (oil that solidified on standing).

Workup

  1. temperaturewas refluxed through a Dean-Stark trap overnight
  2. extractionextracted with 10% aqueous N-methyl-D-glucamine (4×25 mL)
  3. extractionThe last extract
  4. filtrationfiltered
  5. customto give
  6. customrecovered nonanedioic acid (3.8 g)
  7. customto separate overnight
  8. customThe organic layer was evaporated
  9. dissolutionthe residue dissolved in hexane (200 mL)
  10. extractionThe solution was extracted with 10% N-methyl-D-glucamine (2×50 mL) (emulsions
  11. additionby adding a little ethanol)
  12. washThe organic solution was washed with water (1×25 mL)
  13. extractionAfter extraction with dichloromethane-tetrahydrofuran (4:1) (5×10 mL)
  14. dry with materialthe combined extracts were dried (Na2SO4)
  15. filtrationfiltered
  16. customevaporated

Sources & evidence

ORD record
ord-a35ab51007294f89b3fe058e1b991c82
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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