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

HRID 12941Notes

Reaction equation

HRID 12941 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.[CH3:22][O:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28].[OH2:30].[C:31]([O:34][CH2:35][CH3:36])(=O)C.N1[CH:42]=[CH:41]C=CC=1>>[CH3:22][O:23][CH2:24][CH2:25][CH2:26][C:27]([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:41](=[O:30])[CH2:42][CH2:36][CH2:35][O:34][CH3:31])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1)=[O:28]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 8857Ethyl AcetateHCID 10168RheinHCID 127949894-Methoxybutanoyl chloride

Product 1

HCID 112025344,5-Bis(4-methoxybutyryloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Procedure

To a stirred suspension of 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (1 g) in pyridine (30 ml) was added 4-methoxybutyryl chloride (2 g). The reaction was stirred at RT for 2 days, and as TLC indicated that starting acid was still present, a further 2 g of the acid chloride was added. Reaction was complete after a further 2 days at RT. The reaction mixture was evaporated to dryness and stirred in 2M HCl (30 ml) for 30 mins. The resultant crude solid was isolated by filtration. This was then slurried with water (30 ml) followed by ethyl acetate (30 ml). The solid was isolated by filtration and oven dried overnight to give 1.0 g (59%).

Workup

  1. customReaction
  2. waitwas complete after a further 2 days at RT
  3. customThe reaction mixture was evaporated to dryness
  4. stirringstirred in 2M HCl (30 ml) for 30 mins
  5. customThe resultant crude solid was isolated by filtration
  6. customThe solid was isolated by filtration and oven
  7. customdried overnight
  8. customto give 1.0 g (59%)

Sources & evidence

ORD record
ord-73c404b0ec0942aba635c345255846ec
Source dataset
uspto-grants-2010_06
Patent number
US07728035B2

Reaction notes

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