Hydrochloric Acid → HCID 59660097, compound

HRID 1466727Notes

Reaction equation

HRID 1466727 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([CH3:19])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:5]([OH:7])=[O:6].C([O-])([O-])=O.[Na+].[Na+].Cl>C(O)C.O>[OH:18][CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]([CH3:3])([CH3:19])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 85986832HCID 85986832, compound

Product 1

HCID 59660097HCID 59660097, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Sodium borohydride (8.0 g, 0.21 mol) was added in portions to 2,2-dimethyl-8-oxododecanoic acid (27.02 g, 0.11 mol) in ethanol (200 mL), followed by addition of Na2CO3 (5 g) while the reaction mixture was gently refluxed. The reaction mixture was stirred at 40-50° C. for 3.5 h and at 60° C. for 1 h. Water (100 mL) and aqueous HCl (10%, 100 mL) were added. The mixture was extracted with ethyl acetate (3×80 mL). The organic solutions were combined, washed with water (100 mL) and brine (2×50 mL), and dried over MgSO4. The solvent was evaporated and the residue was purified twice by column chromatography (silica gel, ethyl acetate/heptane=1:3). Coevaporation with toluene and drying in high vacuo at 70° C. for 1 h gave 8-hydroxy-2,2-dimethyldodecanoic acid (9.6 g, 35%) as an oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 7.5-6.5 (br, 1H), 3.60 (m, 1H), 1.53-1.29 (m, 17H), 1.21 (s, 6H), 0.91 (t, J=6.6 Hz, 3H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 185.0, 73.0, 43.1, 41.5, 38.2, 38.0, 31.2, 28.8, 26.5, 26.0, 25.9, 23.8, 15.1. HRMS (LSIMS, gly): Calcd for C14H29O3 (MH+): 245.2116. found: 245.2107. HPLC: 97.1% pure. Elemental analysis (C14H28O3): Calcd for C, 68.81; H, 68.67. Found: C, 68.67; H, 11.64.

Workup

  1. temperaturewas gently refluxed
  2. extractionThe mixture was extracted with ethyl acetate (3×80 mL)
  3. washwashed with water (100 mL) and brine (2×50 mL)
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated
  6. customthe residue was purified twice by column chromatography (silica gel, ethyl acetate/heptane=1:3)
  7. dry with materialCoevaporation with toluene and drying in high vacuo at 70° C. for 1 h

Sources & evidence

ORD record
ord-f9e66e14bc5447f39c6daee9ea986696
Source dataset
uspto-grants-2015_04
Patent number
US09000041B2

Reaction notes

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