Acetic Acid → HCID 21191974, compound

HRID 1957806Notes

Reaction equation

HRID 1957806 reaction equation
[OH:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]([OH:17])=[O:16])[CH:8]=2)[CH:3]=1.[C:18](O)(=[O:20])[CH3:19].CN(C)C=O.O>C(OC(=O)C)(=O)C.CN(C)C1C=CN=CC=1.CO>[C:18]([O:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]([OH:17])=[O:16])[CH:8]=2)[CH:3]=1)(=[O:20])[CH3:19]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6228DimethylformamideHCID 98160552-hydroxynaphthalen-3,6-dicarboxylic acid

Product 1

HCID 21191974HCID 21191974, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
50 °C

Procedure

2-Hydroxy-3,6-di-hydroxycarbonylnaphthalene (12.1 g) was suspended in acetic anhydride (39.0 g), acetic acid (60.1 g) and N,N-dimethylformamide (40.0 g) and 4-dimethylaminopyridine (0.2 g) was added, followed by heating to 50° C. After heating for about 20 hours, the reaction solution was poured into a mixed solution of water (400 g) and methanol (100 g). The deposit was filtered and then washed with water to obtain 11.6 g of 2-acetoxy-3,6-di-hydroxycarbonylnaphthalene as grayish white powder (DSC analysis value: 239.2° C.).

Workup

  1. temperatureAfter heating for about 20 hours
  2. filtrationThe deposit was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-d887f46735c54eada6b66bff94f35504
Source dataset
uspto-grants-1998_07
Patent number
US05786523

Reaction notes

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