Acetic Anhydride → HCID 15418433, compound

HRID 1682104Notes

Reaction equation

HRID 1682104 reaction equation
[C:1]1([C:7]([OH:9])=[O:8])([C:4]([OH:6])=[O:5])[CH2:3][CH2:2]1.[C:10]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(OC(=O)C)(=O)C>S(=O)(=O)(O)O>[CH2:3]1[C:1]2([C:7](=[O:9])[O:8][C:10]3([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[O:5][C:4]2=[O:6])[CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 7967CyclohexanoneHCID 690171,1-Cyclopropanedicarboxylic acid

Product 1

HCID 15418433HCID 15418433, compoundYield 12,843.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of cyclopropane-1,1-dicarboxylic acid (13.0 g, 0.10 mmol), cyclohexanone (10.8 g, 0.11 mol), acetic anhydride (11.2 g, 0.11 mol) and concentrated sulphuric acid (5 drops) was stirred at room temperature 0.5 h. The mixture soon became a wine-red solution which later darkened to purple. The reaction mixture was partitioned between water (100 ml) and ether (2×100 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), filtered and evaporated to leave a purple oil plus some solid material. This mixture was purified by column chromatography on silica [eluent=ether/hexane (4:1)] to give the title compound as colourless crystals (2.70 g, 13%), m.p. 134.5°-135° C.

Workup

  1. customThe reaction mixture was partitioned between water (100 ml) and ether (2×100 ml)
  2. washThe combined organic extracts were washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto leave a purple oil
  7. customThis mixture was purified by column chromatography on silica [eluent=ether/hexane (4:1)]

Sources & evidence

ORD record
ord-e4523ab069634d07ba28a0ad80adcfad
Source dataset
uspto-grants-1992_12
Patent number
US05175288

Reaction notes

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