Water → 1,3-Propanediol

HRID 890835Notes

Reaction equation

HRID 890835 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1C=O.[CH2:19]([OH:23])[CH2:20][CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:8]1([CH:21]=[O:22])[C:7]2[C:6](=[O:16])[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[C:13](=[O:15])[C:12]=2[CH:11]=[CH:10][CH:9]=1.[CH2:19]([OH:23])[CH2:20][CH2:21][OH:22]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 3443109,10-Dioxo-9,10-dihydroanthracene-2-carbaldehyde

Product 2

HCID 104421,3-PropanediolHCID 616802HCID 616802, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of anthraquinone-2-aldehyde (12.0 g), 1,3-propanediol (10 ml), and p-toluenesulfonic acid (20 mg) in toluene (300 ml) was heated under reflux with a removal of water formed from the condensation of anthraquinone aldehyde and 1,3-propane diol for 4 hours. The mixture was then cooled to room temperature, filtered off with suction, washed with water and diethyl ether, and dried under vacuum to afford anthraquinone-2-propaneacetal (12.5 g, 84%).

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-80e256c5d38242e3bfcf7e6c21b708e2
Source dataset
uspto-grants-2006_02
Patent number
US06998487B2

Reaction notes

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