2,3-Dihydroxybutanedioic Acid → HCID 12784477, compound

HRID 648234Notes

Reaction equation

HRID 648234 reaction equation
Cl[CH2:2][CH:3]([OH:20])[CH2:4][O:5][C:6]1[C:11]2[CH2:12][CH2:13][C:14]([CH3:19])([CH3:18])[C:15](=[O:17])[CH2:16][C:10]=2[CH:9]=[CH:8][CH:7]=1.C(O)(=O)C(C(C(O)=O)O)O.CCOCC.[C:36]([NH2:40])([CH3:39])([CH3:38])[CH3:37]>O1CCOCC1>[C:36]([NH:40][CH2:2][CH:3]([OH:20])[CH2:4][O:5][C:6]1[C:11]2[CH2:12][CH2:13][C:14]([CH3:19])([CH3:18])[C:15](=[O:17])[CH2:16][C:10]=2[CH:9]=[CH:8][CH:7]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 3283Diethyl EtherHCID 6385Tert-ButylamineHCID 12784476HCID 12784476, compound

Product 1

HCID 12784477HCID 12784477, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,2 g crude 1-(3-chloro-2-hydroxypropoxy)-6,7,8,9-tetrahydro-7,7-dimethyl-5H-benzocyclohepten-6-one in 20 ml dioxane and 10 ml tert-butylamine are heated at 130° for 20 hours in an autoclave. The reaction mixture is divided between 10% (w/w) aqueous tartaric acid solution and ether. The aqueous phase is made alkaline and extracted with ether. Evaporation of the ether phase yields the title compound (M.pt of hydrogen maleate 186°-188° after crystallization from ethanol).

Workup

  1. extractionextracted with ether
  2. customEvaporation of the ether phase

Sources & evidence

ORD record
ord-acbf6370a01d4128be4531fa736ad172
Source dataset
uspto-grants-1983_10
Patent number
US04411913

Reaction notes

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