Hydrochloric Acid → 11-(1-Carboxycyclopropyl)-7-hydroxy-2,2-dimethylundecanoic acid

HRID 563161Notes

Reaction equation

HRID 563161 reaction equation
[C:1]([C:4]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])[CH2:6][CH2:5]1)([OH:3])=[O:2].[OH-].[Na+].[BH4-].[Na+].Cl>CC(O)C.O>[C:1]([C:4]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:20])([CH3:21])[C:17]([OH:19])=[O:18])[CH2:5][CH2:6]1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 1146111411-(1-Carboxycyclopropyl)-2,2-dimethyl-7-oxoundecanoic acid

Product 1

HCID 2193201911-(1-Carboxycyclopropyl)-7-hydroxy-2,2-dimethylundecanoic acidYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a mixture of 11-(1-carboxycyclopropyl)-2,2-dimethyl-7-oxoundecanoic acid (3.63 g, >90% pure by NMR, 10.4 mmol) in iPrOH (20 mL) and H2O (20 mL) was added NaOH (0.94 g, 23.5 mmol). After 5 min of stirring, NaBH4 (0.24 g, 6.3 mmol) was added to the resulting clear solution. After 19 h, the mixture was acidified to pH˜1 with aqueous HCl (2M) and extracted with Et2O (3×50 mL). The combined organic phases were washed with brine (1×50 mL), dried (Na2SO4) and evaporated in vacuo. The remaining residue was coevaporated in vacuo from EtOAc to give 11-(1-carboxycyclopropyl)-7-hydroxy-2,2-dimethylundecanoic acid (3.43 g, 93%, contains 8% (w/w) EtOAc and 3% (w/w) iPrOH) as a viscous colorless oil. 1H NMR (CD3OD): δ=3.5 (br s, 1H), 1.56-1.27 (m, 16H), 1.16 (s, 6H), 1.16-1.14 (m, 2H), 0.72 (dd, J=3.4, 6.6 Hz, 2H). 13C NMR (CD3OD): δ=181.6, 179.1, 72.3, 43.1, 42.0, 38.5, 38.4, 35.2, 29.0, 27.5, 27.1, 26.4, 26.0, 25.9, 24.4, 16.43, 16.38. HRMS calcd for C17H31O5 (M+H+): 315.2171, found 315.2175.

Workup

  1. waitAfter 19 h
  2. extractionextracted with Et2O (3×50 mL)
  3. washThe combined organic phases were washed with brine (1×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-bb7b2e0bd0414c56992edfe44d82af1a
Source dataset
uspto-grants-2011_11
Patent number
US08067466B2

Reaction notes

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