Hydrochloric Acid → HCID 10867593, compound

HRID 1363873Notes

Reaction equation

HRID 1363873 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][O:8][CH2:9][C@H:10]2[CH2:14][O:13]C(C)(C)[O:11]2)=[CH:5][CH:4]=1.Cl.C(=O)([O-])O.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][CH2:9][C@H:10]([OH:11])[CH2:14][OH:13])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 13904786HCID 13904786, compound

Product 1

HCID 10867593HCID 10867593, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude product of (S)-(+)-4-(4-methoxybenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane (4.1 g) was dissolved in methanol (10 mL). The solution was added with 1N hydrochloric acid and stirred at room temperature for one day. The solution was adjusted to pH 6 by addition of saturated sodium hydrogen carbonate, and extracted four times with dichloromethane. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed and the residue was purified by silica gel column chromatography to obtain (R)-(+)-3-(4-methoxybenzyloxy)-1,2-propanediol (2.4 g, 69%).

Workup

  1. extractionextracted four times with dichloromethane
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cebc500d5f7d44ce922c2b4917a07719
Source dataset
uspto-grants-2011_02
Patent number
US07887835B2

Reaction notes

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