Hydrochloric Acid → HCID 11587534, compound

HRID 2057172Notes

Reaction equation

HRID 2057172 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH2:8][C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[CH2:23][OH:24])[C:15](O)=[O:16].O.Cl>C1COCC1>[OH:16][CH2:15][CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[CH2:23][OH:24])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([CH3:28])([CH3:27])[CH2:8][OH:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 117024498-Hydroxy-2-(6-hydroxy-5,5-dimethylhexyl)-7,7-dimethyloctanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11587534HCID 11587534, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen atmosphere, to a solution of lithium aluminum hydride (1.09 g, 28.8 mmol) in anhydrous THF (100 mL) was added dropwise a solution of 8-hydroxy-2-(6-hydroxy-5,5-dimethylhexyl)-7,7-dimethyloctanoic acid (3.64 g, 11.5 mmol) in THF (40 mL) at room temperature. The reaction mixture was heated at reflux for 5 h and kept at room temperature overnight. Water (100 mL) was added carefully to the reaction mixture under cooling with a water bath. The pH was adjusted to 1 with 2 N hydrochloric acid. The product was extracted with diethyl ether (3×60 mL). The combined organic layers were washed with water (2×50 mL) and brine (50 mL). The ethereal solution was dried over sodium sulfate and concentrated in vacuo to furnish the crude product (3.2 g), which was purified by chromatography on silica (hexanes:ethyl acetate=50:50) to yield 7-hydroxymethyl-2,2,12,12-tetramethyltridecane-1,13-diol (3.0 g, 86%) as a yellow oil. 1H NMR (300 MHz, CD3OD/TMS): δ (ppm): 4.88 (s, 3H), 3.44 (d, 2H, J=4.8 Hz), 3.23 (s, 4H), 1.5-1.1 (m, 17H), 0.85 (s, 12H). 13C NMR (75 MHz, CD3OD/TMS): δ (ppm): 72.0, 65.7, 41.7, 40.0, 36.0, 32.2, 29.0, 25.4, 24.7, 24.6. HRMS (LSIMS, gly): Calcd. for C18H39O3 (MH+): 303.2899, found 303.2901. HPLC: 94.6% purity.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. temperatureunder cooling with a water bath
  4. extractionThe product was extracted with diethyl ether (3×60 mL)
  5. washThe combined organic layers were washed with water (2×50 mL) and brine (50 mL)
  6. dry with materialThe ethereal solution was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto furnish the crude product (3.2 g), which
  9. customwas purified by chromatography on silica (hexanes:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-518a9fe98f754e72af90aa23c15ec27a
Source dataset
uspto-grants-2008_02
Patent number
US07335799B2

Reaction notes

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