Water → Nonanoic acid, 9-hydroxy-, methyl ester

HRID 5256

Reaction equation

HRID 5256 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12].O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)C>[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])([O:2][CH3:1])=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 75009Monomethyl azelate

Product 1

HCID 292983Nonanoic acid, 9-hydroxy-, methyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 165 mL (165 mmol) of a 1.0M solution of boranetetrahydrofuran complex in tetrahydrofuran in 200 mL of dry diethyl ether at 0° C. is added dropwise 25.0 g (123 mmol) of azelaic acid monomethyl ester, added at such a rate as to prevent excessive release of gas and exothermicity. The solution is allowed to warm to room temperature overnight and is worked up by slowly adding water until gas evolution ceases. Then solid potassium carbonate is added and the organic layer is separated. The aqueous layer is extracted three times with diethyl ether. The combined extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 8-carbomethoxyoctan-1-ol as a colorless oil.

Workup

  1. additionadded at such a rate as
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is extracted three times with diethyl ether
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-052d6b3cc80f4fa28f5010b0d03ff42b
Source dataset
uspto-grants-1993_09
Patent number
US05242945

Linked notes

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