Hydrochloric Acid → HCID 131712413, compound

HRID 1577796Notes

Reaction equation

HRID 1577796 reaction equation
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[Cl:14][CH:15]([Cl:28])[C:16]([C@H:18]1[C@H:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]1([CH3:27])[CH3:26])=[O:17].Cl>C(O)(C)C>[Cl:14][CH:15]([Cl:28])[CH:16]([C@H:18]1[C@H:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]1([CH3:27])[CH3:26])[OH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 131712414HCID 131712414, compound

Product 1

HCID 131712413HCID 131712413, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Aluminium isopropoxide (0.97 g, 0.005 M) and (±) trans ethyl 3-dichloroacetyl-2,2-dimethylcyclopropane-1-carboxylate (1.0 g, 0.004 M) were refluxed in isopropanol (6.0 ml) for 16 hours. On cooling, the mixture was poured into 2 N hydrochloric acid (50 ml) and then extracted with ether (3×30 ml). The combined organic layers were extracted with water (2×50 ml), dried and evaporated in vacuo to yield a colourless oil. This product was identical (n.m.r. and i.r. spectra and g.l.c.) to the title product obtained from the sodium borohydride reduction described above in Example 3.

Workup

  1. temperatureOn cooling
  2. extractionextracted with ether (3×30 ml)
  3. extractionThe combined organic layers were extracted with water (2×50 ml)
  4. customdried
  5. customevaporated in vacuo
  6. customto yield a colourless oil

Sources & evidence

ORD record
ord-78fa0017eea6480684d4878fe1de621a
Source dataset
uspto-grants-1981_09
Patent number
US04289711

Reaction notes

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