Sulfuric Acid → HCID 21477262, compound

HRID 2293699Notes

Reaction equation

HRID 2293699 reaction equation
[C:1]([CH:4]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:12])([OH:3])=[O:2].C(O[C:17](=O)[CH3:18])(=O)C.S(=O)(=O)(O)O.[C:25]([O-])(O)=O.[Na+]>CC(C)=O>[CH3:25][C:17]1([CH3:18])[O:2][C:1](=[O:3])[C:4]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[O:12]1

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 214772122-Oxocyclooctane-1-carboxylic acid

Product 1

HCID 21477262HCID 21477262, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 2-carboxycyclooctanone of Preparation 86 (16.8 g) is added acetone (15 mL), acetic anhydride (20 mL) and sulfuric acid (0.8 mL, added dropwise) at 0° C. As soon as the sulfuric acid is added the solid dissolved and stirring continued for 1 hour at 0° C. and then the reaction is placed in the refrigerator (4° C.) overnight. The reaction is poured into NaHCO3 (500 mL) containing ice and then stirred for 1 hour at room temperature. The solid is collected on a filter and washed with water and air dried to yield 10.50 g of the product. Recrystallization from ether affords 8.9 g of the title product.

Workup

  1. additionadded dropwise) at 0° C
  2. dissolutiondissolved
  3. customis placed in the refrigerator (4° C.) overnight
  4. additioncontaining ice
  5. stirringstirred for 1 hour at room temperature
  6. customThe solid is collected on
  7. filtrationa filter
  8. washwashed with water and air
  9. customdried

Sources & evidence

ORD record
ord-7f432668b75d482b80426e8fbb19bddd
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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