Water → 4,5-Bis(2-benzyloxyacetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

HRID 12940Notes

Reaction equation

HRID 12940 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1.[CH2:22]([O:29][CH2:30][C:31](Cl)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:34]([O:37][CH2:38][CH3:39])(=O)[CH3:35].ClCCl.[OH2:43]>N1C=CC=CC=1>[CH2:22]([O:29][CH2:30][C:31]([O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[O:17][C:35](=[O:43])[CH2:34][O:37][CH2:38][C:39]3[CH:6]=[CH:15][CH:2]=[CH:3][CH:4]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 10168RheinHCID 177085Benzyloxyacetyl chloride

Product 1

HCID 114559804,5-Bis(2-benzyloxyacetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4,5-Dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (3.0 g) was suspended in pyridine (100 ml) and stirred at RT for 30 mins. Benzyloxyacetyl chloride (3.6 g, 5 equiv.) was added, to give a clear reaction mixture which was stirred at RT over the weekend. The reaction mixture was reduced to a smaller volume and quenched with 2M HCl (200 ml), adjusting the pH to pH 2. An orange solid was isolated by filtration. This crude solid was slurried in water (30 ml), followed by ethyl acetate (30 ml) and dichloromethane (30 ml). A yellow solid was isolated by filtration (3.6 g, 61%).

Workup

  1. customto give a clear reaction mixture which
  2. stirringwas stirred at RT over the weekend
  3. customquenched with 2M HCl (200 ml)
  4. customAn orange solid was isolated by filtration
  5. customA yellow solid was isolated by filtration (3.6 g, 61%)

Sources & evidence

ORD record
ord-ba0d0475fac4495ead26baa58c66eb98
Source dataset
uspto-grants-2010_06
Patent number
US07728035B2

Reaction notes

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