Acetic Acid → HCID 14726499, compound

HRID 1728470Notes

Reaction equation

HRID 1728470 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-49d30f68fd2c41de8901b9df63726e28
Source dataset
uspto-grants-1994_07
Patent number
US05326900

Reaction notes

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