Hydrochloric Acid → HCID 59660140, compound

HRID 2057206Notes

Reaction equation

HRID 2057206 reaction equation
C([O:3][C:4](=O)[C:5]([CH3:18])([CH3:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.Cl>CCOCC>[CH3:18][C:5]([CH3:17])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:16])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 85986822HCID 85986822, compound

Product 1

HCID 59660140HCID 59660140, compoundYield 810.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,2-dimethyl-8-oxododecanoic acid ethyl ester (14.33 g, 5.3 mmol) in Et2O (30 mL) was added to a suspension of LiAlH4 (4.6 g, 12 mmol) in Et2O (200 mL). The reaction mixture was heated to reflux for 2 h. Water (100 mL) and aqueous HCl (10%, 200 mL) were added. The aqueous solution was separated and extracted with Et2O (2×100 mL). The combined organic solutions were washed with saturated, aqueous NaHCO3 solution (100 mL) and brine (50 mL) and dried over MgSO4. The solvent was evaporated and the residue was purified by column chromatography (silica gel, ethyl acetate/hexanes=1:10, 200 mL, then 1:3, 150 mL) to yield 2,2-dimethyldodecan-1,8-diol (9.9 g, 81%) as a colorless oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 3.55 (br s, 1H), 3.29 (s, 2H), 1.7 (br. s, 2H), 1.42-1.20 (m, 16H), 0.89 (t, J=7.2 Hz, 3H), 0.84 (s, 6H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 72.1, 72.0, 38.7, 37.6, 37.3, 35.2, 30.8, 28.0, 25.8, 24.0, 23.9, 22.9, 14.3. HRMS (LSIMS, gly): Calcd for C14H31O2 (MH+): 231.2324, found: 231.2324. HPLC: 99.8% pure. Elemental analysis (C14H30O2): Calcd for C, 72.99; H, 13.12. Found: C, 72.75; H, 13.23.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe aqueous solution was separated
  4. extractionextracted with Et2O (2×100 mL)
  5. washThe combined organic solutions were washed with saturated, aqueous NaHCO3 solution (100 mL) and brine (50 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography (silica gel, ethyl acetate/hexanes=1:10, 200 mL

Sources & evidence

ORD record
ord-e4df36481b75422894c38bdbac11841b
Source dataset
uspto-grants-2008_02
Patent number
US07335799B2

Reaction notes

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