Hydrochloric Acid → 2-Acetyl-7-(allyloxybutyloxy)fluorene

HRID 130273Notes

Reaction equation

HRID 130273 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([OH:17])=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[CH2:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25]Cl)[CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([O:17][CH2:25][CH2:24][CH2:23][CH2:22][O:21][CH2:18][CH:19]=[CH2:20])=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 8219132-Acetyl-7-hydroxyfluoreneHCID 137481731-Chloro-4-[(prop-2-en-1-yl)oxy]butane

Product 1

HCID 692519582-Acetyl-7-(allyloxybutyloxy)fluoreneYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Acetyl-7-hydroxyfluorene 22.4 g, allyl(4-chlorobutyl) ether 18 g and potassium carbonate 20 g were added to dimethylformamide 150 ml and stirred at 90° C. for 8 hours. The reaction mixture was poured into 6N hydrochloric acid 300 ml to obtain a solid matter. The solid matter was filtered and dried, and then it was recrystallized from ethanol to obtain 22 g of 2-acetyl-7-(allyloxybutyloxy)fluorene. The melting point was 77° C.

Workup

  1. customto obtain a solid matter
  2. filtrationThe solid matter was filtered
  3. customdried
  4. customit was recrystallized from ethanol

Sources & evidence

ORD record
ord-9df82e5502bc473eb5ad15896a975d0f
Source dataset
uspto-grants-2008_06
Patent number
US07381350B2

Reaction notes

Loading…