Sulfuric Acid → HCID 59659473, compound

HRID 1175005Notes

Reaction equation

HRID 1175005 reaction equation
[CH3:1][C:2]([CH3:34])([CH2:11][CH2:12][CH2:13][CH:14]([OH:33])[CH2:15][CH2:16][CH:17]([OH:32])[CH2:18][CH2:19][CH2:20][C:21]([CH3:31])([CH3:30])[CH2:22][O:23]C1CCCCO1)[CH2:3][O:4]C1CCCCO1.S(=O)(=O)(O)O>CO>[CH3:30][C:21]([CH3:31])([CH2:20][CH2:19][CH2:18][CH:17]([OH:32])[CH2:16][CH2:15][CH:14]([OH:33])[CH2:13][CH2:12][CH2:11][C:2]([CH3:1])([CH3:34])[CH2:3][OH:4])[CH2:22][OH:23]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 11248763HCID 11248763, compound

Product 1

HCID 59659473HCID 59659473, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,2,13,13-tetramethyl-1,14-bis(tetrahydropyran-2-yloxy)tetradecane-6,9-diol (5.07 g, 0.01 mol) in methanol (100 mL) was treated with dilute aqueous sulfuric acid (5 mL of concentrated sulfuric acid in 15 mL of water), and stirred at room temperature overnight. The methanol was removed under reduced pressure and the residue was extracted with ethyl acetate (100 mL). The aqueous phase was saturated with solid sodium chloride and extracted again with ethyl acetate (75 mL). The combined organic extracts were washed with a saturated sodium chloride solution (50 mL) and dried over magnesium sulfate. The solid obtained after solvent removal was washed with diethyl ether (10 mL) to give 2,2,13,13-tetramethyltetradecan-1,6,9,14-tetraol (1.85 g, 58%) as a white powder. M.p.: 96-97° C. 1H NMR (300 MHz, DMSO-d6/TMS): δ (ppm): 4.42 (pseudo-t, 2 H, J=5.0 Hz), 4.28 (pseudo-t, 2 H, J=5.0 Hz), 3.37-3.34 (m, 2 H), 3.06 (d, 4H, J=5.0 Hz), 1.47-1.08 (m, 16 H), 0.77 (s, 12 H). 13C NMR (75 MHz, DMSO-d6/TMS): δ (ppm): 70.1, 69.9, 38.8, 38.4, 34.9, 33.7, 24.2, 19.7. HRMS (LSIMS, nba): Calcd. for C19H39O4 (MH+): 319.2843. found: 319.2853.

Workup

  1. customThe methanol was removed under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate (100 mL)
  3. extractionextracted again with ethyl acetate (75 mL)
  4. washThe combined organic extracts were washed with a saturated sodium chloride solution (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe solid obtained
  7. customafter solvent removal
  8. washwas washed with diethyl ether (10 mL)

Sources & evidence

ORD record
ord-73e72f2115fd4518979bfde201500c5e
Source dataset
uspto-grants-2010_11
Patent number
US07838554B2

Reaction notes

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