Hydrochloric Acid → 2-(4-Benzyloxyphenoxy)propane-1,3-diol

HRID 1260505Notes

Reaction equation

HRID 1260505 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][CH:24]([C:29](OC)=[O:30])[C:25](OC)=[O:26])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C1(C)C=CC=CC=1>[CH2:11]([O:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][CH:24]([CH2:29][OH:30])[CH2:25][OH:26])=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 67071604Dimethyl 2-(4-benzyloxyphenoxy)malonate

Product 1

HCID 498554052-(4-Benzyloxyphenoxy)propane-1,3-diol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminum hydride (7.08 ml) was slowly added dropwise to dimethyl 2-(4-benzyloxyphenoxy)malonate (477 mg, 1.44 mmol) in 16 ml of toluene under argon at 0° C. The reaction mixture was stirred at 0° C. for 2 h and, after addition of 1M hydrochloric acid solution, extracted with ethyl acetate. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 98.6 mg (25%), M+H+: 275.20.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was separated off
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-1f0fd577abe849fb808ef6655844703d
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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