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

HRID 1263947Notes

Reaction equation

HRID 1263947 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].ClC(OCC)=O.[BH4-].[Na+].CO>O1CCCC1.O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]

Participants

7

Reactant 4

HCID 887MethanolHCID 10928Ethyl chloroformateHCID 75009Monomethyl azelateHCID 4311764Sodium borohydride

Product 1

HCID 292983Nonanoic acid, 9-hydroxy-, methyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Azelaic acid monomethyl ester (20 mmole) was dissolved in tetrahydrofuran (100 mL) and kept in argon atmosphere at −10° C. Trietbylamine (30 mmole) was added dropwise to the reaction flask, followed by the addition of ethyl chloroformate (25 mmole). The solution was stirred for 20 minutes, and sodium borohydride (60 mmole) was added in one portion. Methanol (40 mL) was added dropwise and the reaction flask was kept at 0° C. for 40 minutes. Water (20 mL) was added and organic solvent was removed by rotavap. The residue was brought to water and ethyl acetate for partition. The organic layer was collected and dried to obtain 9-hydroxy-nonanoic acid methyl ester in decent purity for use in Step 4. The yield is >90%.

Workup

  1. customat −10° C
  2. additionTrietbylamine (30 mmole) was added dropwise to the reaction flask
  3. waitthe reaction flask was kept at 0° C. for 40 minutes
  4. customorganic solvent was removed by rotavap
  5. customfor partition
  6. customThe organic layer was collected
  7. customdried

Sources & evidence

ORD record
ord-828333c68a8d4130b1083814305f9d78
Source dataset
uspto-grants-2003_04
Patent number
US06541506B1

Reaction notes

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