Hydrochloric Acid → HCID 67301835, compound

HRID 1015357Notes

Reaction equation

HRID 1015357 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=O>C(O)=O.[Zn]>[Cl:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][CH:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178525726HCID 178525726, compound

Product 1

HCID 67301835HCID 67301835, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

In a 50 ml beaker, Zn dust (3.6 g; 54 mmol) was added to 1N HCl and mixture was stirred with a glass rod. Aqueous was decanted off and solids were added to a mixture of trans-4-(3-chlorobenzoyl)cyclohexane-1-carboxylic acid (718 mg; 2.69 mmol) in 30 mL of formic acid. Mixture was heated to reflux for 2 hours. The reaction was cooled to room temperature and white solids were filtered off and rinsed with diethyl ether. Filtrate was concentrated and residue was taken up in a 40 mL mixture of diethyl ether and water (1:1). Organics were separated and aqueous was re-extracted with 2×20 mL of diethyl ether. Combined organics were washed with sat. NaHCO3, water, brine, and dried over MgSO4. Title compound was obtained as a crude oil. 550 mg (81% crude yield).

Workup

  1. customAqueous was decanted off
  2. temperatureMixture was heated
  3. temperatureto reflux for 2 hours
  4. filtrationwhite solids were filtered off
  5. washrinsed with diethyl ether
  6. concentrationFiltrate was concentrated
  7. customOrganics were separated
  8. extractionaqueous was re-extracted with 2×20 mL of diethyl ether
  9. washCombined organics were washed with sat. NaHCO3, water, brine
  10. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d1ff7a3abc8d4ef484b8f99bc343128e
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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