Acetic Acid → HCID 14726499, compound

HRID 1614098Notes

Reaction equation

HRID 1614098 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:28])[C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=3[CH:15]=2)=[O:13])=[CH:7][CH:6]=1)([O:3]C)=[O:2].C(O)(=O)C.O>S(=O)(=O)(O)O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:28])[C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:20]([CH3:24])([CH3:25])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=3[CH:15]=2)=[O:13])=[CH:7][CH:6]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962Water2×HCID 14726493HCID 14726493, compound

Product 1

HCID 14726499HCID 14726499, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3.9 g (10 mmol) of 1-(4-Carbomethoxyphenyl)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethanedione (Example 6) were refluxed in a mixture of 5 ml of concentrated sulfuric acid, 80 ml of glacial acetic acid and 40 ml of water for 8 h. The mixture was then poured into 500 ml of water, and the crystalline precipitate was filtered off with suction and washed with water until the washings were neutral. The dried crude product was recrystallized from cyclohexane, yielding 3.1 g of the title compound of melting point 148°-151° C.

Workup

  1. filtrationthe crystalline precipitate was filtered off with suction
  2. washwashed with water until the washings
  3. customThe dried crude product
  4. customwas recrystallized from cyclohexane

Sources & evidence

ORD record
ord-f5b99b94191a4e9da3c4a931be74d914
Source dataset
uspto-grants-1993_03
Patent number
US05194664

Reaction notes

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