9-Decen-1-ol → 2-Propenoic acid, 3-(2-hydroxyphenyl)-, 9-decen-1-yl ester, (2E)-

HRID 655070

Reaction equation

HRID 655070 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH3:2].[CH2:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]C=C>CCOCC>[CH2:1]([O:3][C:4](=[O:14])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH2:2][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

4

Reactant 2

HCID 256129-Decen-1-olHCID 576496Ethyl 3-(2-hydroxyphenyl)prop-2-enoate

Product 1

HCID 177820092-Propenoic acid, 3-(2-hydroxyphenyl)-, 9-decen-1-yl ester, (2E)-Yield 21.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5.0 g 3-(2-hydroxy-phenyl)-acrylic acid ethyl ester, 6.1 g dec-9-en-1-ol and 1.0 g tetraisopropyl-ortho-titanate was heated to 150° C. removing the ethanol formed. After stirring for 2.5 hours at this temperature, the reaction mixture was cooled, diluted with ether and washed with brine. The organic phase was dried and evaporated to dryness. The resulting oil was Kugelrohr-distilled, crystallized and recrystallized to yield 1.69 g of colourless crystals.

Workup

  1. customremoving the ethanol
  2. customformed
  3. temperaturethe reaction mixture was cooled
  4. washwashed with brine
  5. customThe organic phase was dried
  6. customevaporated to dryness
  7. distillationThe resulting oil was Kugelrohr-distilled
  8. customcrystallized
  9. customrecrystallized

Sources & evidence

ORD record
ord-ff72df1e00034eddb3180f5fcfb72700
Source dataset
uspto-grants-2011_12
Patent number
USRE043006E1

Linked notes

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