1-Butanol → Flurenol-butyl

HRID 898512Notes

Reaction equation

HRID 898512 reaction equation
[OH:1][C:2]1([C:15]([OH:17])=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH2:18](O)[CH2:19][CH2:20][CH3:21].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[OH:1][C:2]1([C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

7

Reactant 4

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 10087FlurenolHCID 516892Sodium Bicarbonate

Product 1

HCID 40816Flurenol-butylYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a reactor were added 0.05 mol of 9-hydroxyfluorene-9-carboxlic acid, 0.075 mol of butanol, 40 ml of toluene and 0.4 ml of concentrated sulfuric acid. The reaction was heated to reflux for 6 hrs, while water was separated by a water segregator. At the end of the reaction, the reaction mixture was neutralized with sodium bicarbonate, washed with saturated saline, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. Removing the solvent gave the product with a yield of 80%.

Workup

  1. temperatureThe reaction was heated
  2. customwas separated by a water segregator
  3. customAt the end of the reaction
  4. washwashed with saturated saline
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoving the solvent
  8. customgave the product with a yield of 80%

Sources & evidence

ORD record
ord-a14efb34ff5e41a38a37228633a5d75f
Source dataset
uspto-grants-2008_04
Patent number
US07351778B2

Reaction notes

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