Dimethyl Sulfoxide → 9,10-Anthracenedicarboxaldehyde

HRID 2057557

Reaction equation

HRID 2057557 reaction equation
[OH:1][CH2:2][C:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2.C(N(CC)CC)C.CS(C)=O>O>[CH:8]1[C:9]2[C:4](=[C:3]([CH:2]=[O:1])[C:16]3[C:11]([C:10]=2[CH:17]=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 376503610-(Hydroxymethyl)anthracene-9-carbaldehyde

Product 1

HCID 815009,10-Anthracenedicarboxaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.20 g. of 10-hydroxymethyl-9-anthracenecarboxaldehyde in a mixture of 14 ml. of triethylamine and 20 ml. of dry dimethylsulfoxide is added a solution of 4.80 g. of sulfur trioxide pyridine complex in 25 ml. of dry dimethylsulfoxide. The mixture is stirred for 50 minutes and then poured into 200 ml. of water. The crystals are collected and washed with water, giving 1.18 g. of the desired product as orange crystals, mp. 224°-245° C.

Workup

  1. additionpoured into 200 ml
  2. customThe crystals are collected
  3. washwashed with water
  4. customgiving 1.18 g

Sources & evidence

ORD record
ord-297aa3b8340041b7a26a71c1d989eae5
Source dataset
uspto-grants-1980_07
Patent number
US04211726

Linked notes

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