1,3-Propanediol → HCID 19738634, compound

HRID 2255817Notes

Reaction equation

HRID 2255817 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].CC([O-])(C)C.[K+].Cl[C:13]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH:27]=[O:28])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[CH:18]2>O>[OH:4][CH2:3][CH2:2][CH2:1][O:5][C:13]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH:27]=[O:28])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[CH:18]2

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 8270310-Chloro-9-anthraldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 19738634HCID 19738634, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1 L 3-necked RB flask equipped with overhead stirrer, condenser, thermometer and N2 inlet line with bubbler was added 1,3-propanediol (Aldrich, 500 mL) and KOt-Bu (MCB, 14.03 g, 0.125 mol). After stirring for 30 min 10-chloro-9-anthracenecarbaldehyde (Aldrich, 25.0 g, 0.104 mol) was added to the flask and the mixture further stirred at 90° for 2.5 h. The reaction mixture was poured into H2O (5 L), filtered, dissolved in EtOAc, washed with H2O (3×500 mL), dried (Na2SO4), filtered and the solvent removed to give 24.98 g of dark oil. This was divided into two portions and each purified by preparative HPLC using SiO2 columns and EtOAc/CH2Cl2 (1:9) as the eluting solvent. Combination of the appropriate fractions followed by removal of the solvents by rotary evaporation gave 19.8 g (66%) of an orange solid, 10-[(3-hydroxy)propoxy]-9-anthracenecarbaldehyde, mp 72°-73°, (C,H).

Workup

  1. customTo a 1 L 3-necked RB flask equipped with overhead stirrer, condenser
  2. additionwas added to the flask
  3. filtrationfiltered
  4. dissolutiondissolved in EtOAc
  5. washwashed with H2O (3×500 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent removed

Sources & evidence

ORD record
ord-4883c2e7bb944142b1ac4a5d74cf21a7
Source dataset
uspto-grants-1993_08
Patent number
US05241107

Reaction notes

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