Tetrahydrofurfuryl alcohol → Tetrahydrofurfuryl 2-(p-prenylphenyl)propionate

HRID 904925Notes

Reaction equation

HRID 904925 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].[CH2:17](O)[CH:18]1[O:22][CH2:21][CH2:20][CH2:19]1>C1CCCCC1.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.C.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH3:16])[C:13]([O:15][CH2:17][CH:18]2[O:22][CH2:21][CH2:20][CH2:19]2)=[O:14])=[CH:10][CH:11]=1)[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 7360Tetrahydrofurfuryl alcoholHCID 1754602-(4-(3-Methyl-2-butenyl)phenyl)propionic acid

Product 1

HCID 13118087Tetrahydrofurfuryl 2-(p-prenylphenyl)propionateYield 81.1%

Reagents, catalysts & solvents 2

HCID 73357732Sulfuric acid, compd. with graphite (7:48)CatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of 21.8 g of 2-(p-prenylphenyl)propionic acid, 10.2 g of tetrahydrofurfuryl alcohol and 0.4 g of graphite bisulfate in 100 ml of cyclohexane was stirred at room temperature for 8 hours. The mixture was passed through a column of silica gel, and the solvent was evaporated to give 24.5 g of tetrahydrofurfuryl 2-(p-prenylphenyl)propionate. b.p. 135° C./0.08 mmHg, IR νmaxneat ; 1730 cm-1.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c363416c890f45c3b17a721d4112681f
Source dataset
uspto-grants-1983_12
Patent number
US04420631

Reaction notes

Loading…