Hydrochloric Acid → HCID 10867593, compound

HRID 2222726Notes

Reaction equation

HRID 2222726 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), added with 1 N hydrochloric acid and stirred at room temperature for one day. The reaction solution was adjusted to pH 6 by addition of saturated aqueous sodium hydrogencarbonate and extracted four times with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The residue was purified by silica gel column chromatography to obtain (R)-(+)-3-(4-methoxybenzyloxy)-1,2-propanediol (2.4 g, yield: 69%).

Workup

  1. extractionextracted four times with dichloromethane
  2. dry with materialThe 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-afd5269ad066409ab70f194ff8e54568
Source dataset
uspto-grants-2008_05
Patent number
US07371877B2

Reaction notes

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