1-Octanol → HCID 69239783, compound

HRID 2172345Notes

Reaction equation

HRID 2172345 reaction equation
[C:1]([OH:12])(=[O:11])[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C1(C)C=CC=CC=1.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>[CH2:13]([O:11][C:1](=[O:12])[CH:2]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:3][OH:4])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 9571-OctanolHCID 10726Tropic acid

Product 1

HCID 69239783HCID 69239783, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 71586775BentoniteCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 49.9 g (300 mmol) of tropic acid and 5.00 g of montmorillonite K10 in 200 ml of toluene is added dropwise at 110° C. 104 g (800 mmol) of 1-octanol. The reaction mixture is stirred for 8 hours, and then toluene/water are removed by azeotropical distillation. The catalyst residue is filtered off and the filtrate is evaporated to dryness to afford 60.4 g (72%) of 3-hydroxy-2-phenyl-propionic acid octyl ester.

Workup

  1. additionis added dropwise at 110° C
  2. customtoluene/water are removed by azeotropical distillation
  3. filtrationThe catalyst residue is filtered off
  4. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-3e682070d4b147b7b7d26d12375c4198
Source dataset
uspto-grants-2015_06
Patent number
US09051448B2

Reaction notes

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