Hydrochloric Acid → 2-benzyloxymethyl-propane-1,3-diol

HRID 546166Notes

Reaction equation

HRID 546166 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15]COC(C)(C)O1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:19](=O)(O)[O-:20].[Na+].C[OH:25]>>[CH2:1]([O:8][CH2:9][CH:10]([CH2:15][OH:25])[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 67189694HCID 67189694, compound

Product 1

HCID 102417822-benzyloxymethyl-propane-1,3-diolYield 95%

Conditions

Temperature
25 °C

Procedure

Benzyloxymethyl-2,2-dimethyl-[1,3]dioxane (5.54 g, 23.44 mmol) was dissolved in methanol (20 ml) and then 3N hydrochloric acid (3 ml) was added. The reaction was stirred at 25° C. for 30 min. After this point the pH was adjusted to 8 with solid sodium bicarbonate and evaporated. The residue was dissolved in ethyl acetate, filtered through a short silica gel pad, washed with ethyl acetate and concentrated in vacuo to afford 2-benzyloxymethyl-propane-1,3-diol (4.39 g, 95%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ ppm 1.99-2.07 (m, 1H, CH), 2.74 (s, 2H, 2×OH), 3.60 (d, J=5.7 Hz, 2 H, OCH2), 3.78 (d, J=5.4 Hz, 4H, 2×OCH2), 4.50 (s, 2H, OCH2Ar), 7.25-7.38 (m, 5H, Ar).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. filtrationfiltered through a short silica gel pad
  4. washwashed with ethyl acetate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b62770f18824682ae5339870b549ef1
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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