Hydrochloric Acid → HCID 68008293, compound

HRID 535157Notes

Reaction equation

HRID 535157 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][C:7]1([CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])[C:19]2[CH:18]=[C:17]([C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][C:10]([C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:11][CH:12]=2)C.[OH-].[Na+].Cl>O>[C:36]([CH2:35][CH2:34][C:7]1([CH2:6][CH2:5][C:4]([OH:41])=[O:3])[C:19]2[CH:18]=[C:17]([C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][C:10]([C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:11][CH:12]=2)([OH:38])=[O:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68008936HCID 68008936, compound

Product 1

HCID 68008293HCID 68008293, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2-neck 250-mL round bottom flask was equipped with a condenser, a nitrogen inlet, and a magnetic stirrer. The flask was charged with 3-[9-(2-ethoxycarbonyl-ethyl)-2,7-dihexanoyl-9H-fluoren-9-yl]-propionic acid ethyl ester (10.76 g), 100 mL of water and 5.0 g of sodium hydroxide. The mixture was then heated to reflux overnight. The reaction mixture was cooled to ambient temperature and acidified to pH=1 by addition of 6N hydrochloric acid solution. The resulting solid was isolated by filtration and washed with three portions of water. The solid was dried under vacuum at 70° C. to give 8.5 g of the title compound. 1H NMR (CDCl3, 300 MHz) δ 8.02-7.98 (m, 4H), 7.82 (m, 2H), 2.99 (t, J=7.6 Hz, 4H), 2.47 (m, 4H), 1.74 (m, 4H), 1.53 (m, 4H), 1.40-1.34 (m, 8H), 0.91 (m, 6H).

Workup

  1. customA 2-neck 250-mL round bottom flask was equipped with a condenser, a nitrogen inlet, and a magnetic stirrer
  2. temperatureThe mixture was then heated
  3. temperatureto reflux overnight
  4. customThe resulting solid was isolated by filtration
  5. washwashed with three portions of water
  6. customThe solid was dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-5e6b6da06c374e82931fc17a2bf19fbc
Source dataset
uspto-grants-2014_10
Patent number
US08854730B2

Reaction notes

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