Phosphoric Acid → 3-(Benzyloxy)-1,2-propanediol

HRID 2113064Notes

Reaction equation

HRID 2113064 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][O:13]C(C)(C)[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(=O)(O)(O)O.[OH-].[Na+]>O>[CH2:1]([O:8][CH2:9][CH:10]([OH:11])[CH2:14][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 857952,2-Dimethyl-4-((phenylmethoxy)methyl)-1,3-dioxolane

Product 1

HCID 980723-(Benzyloxy)-1,2-propanediol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 222 g (1.0 mol) of 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane was added 400 g of distilled water, and the whole was adjusted to pH 2 with phosphoric acid. With introduction of nitrogen thereinto, the solution was heated to 70° C. After 2 hours of reaction, the solution was adjusted to pH 7.0 with sodium hydroxide. Thereto was charged 1 L of chloroform and extraction was carried out. Then, the chloroform layer was dried over magnesium sulfate and concentrated. Thereafter, the concentrate was filtrated to remove salts, and thereby 3-benzyloxy-1,2-propanediol was obtained. The NMR data thereof are the same as those in Example 1-2.

Workup

  1. customAfter 2 hours of reaction
  2. additionThereto was charged
  3. extraction1 L of chloroform and extraction
  4. dry with materialThen, the chloroform layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. filtrationThereafter, the concentrate was filtrated
  7. customto remove salts

Sources & evidence

ORD record
ord-3af6a777c9484ba4ac719e3bb84d56ba
Source dataset
uspto-grants-2009_04
Patent number
US07524875B2

Reaction notes

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