Water → 3-Ethoxy-4-hydroxybenzyl 8-methylnonanoate

HRID 1012888Notes

Reaction equation

HRID 1012888 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH2:7][OH:8])[CH3:2].[CH3:13][CH:14]([CH3:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](O)=[O:22].O>CCCCCC>[CH3:13][CH:14]([CH3:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:11]([OH:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 1114708-Methylnonanoic acidHCID 597767Ethyl vanillyl alcohol

Product 1

HCID 673169933-Ethoxy-4-hydroxybenzyl 8-methylnonanoateYield 89.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

3-Ethoxy-4-hydroxybenzyl alcohol (733 mg, 4.35 mmol), 8-methylnonanoic acid (751 mg, 4.35 mmol) and Novozyme 435 (100 mg) were measured and placed in a flask (25 ml). The mixture was stirred with heating in an oil bath at 50° C. for 16 hr without plugging the flask. After stirring with heating for 2 to 3 hr, attachment of water onto the upper wall of the flask was observed. The reaction mixture was allowed to cool to room temperature, hexane (50 ml) was added, and Novozyme 435 and the insoluble material were removed by filtration. Hexane (25 ml) was added to the filtrate, and the mixture was washed with 5% aqueous citric acid solution (25 ml×2) and saturated brine (25 ml) and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure to give 3-ethoxy-4-hydroxybenzyl 8-methylnonanoate (1.25 g, yield 88.8%) as a colorless oil.

Workup

  1. customplaced in a flask
  2. stirringAfter stirring
  3. temperaturewith heating for 2 to 3 hr
  4. temperatureto cool to room temperature
  5. customNovozyme 435 and the insoluble material were removed by filtration
  6. additionHexane (25 ml) was added to the filtrate
  7. washthe mixture was washed with 5% aqueous citric acid solution (25 ml×2) and saturated brine (25 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationMagnesium sulfate was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-663edc46763747b4ab38b2ebb736dff6
Source dataset
uspto-grants-2011_07
Patent number
US07981460B2

Reaction notes

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