Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

HRID 326109

Reaction equation

HRID 326109 reaction equation
[CH2:1]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([CH:8]([CH2:9][OH:10])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 69090Diethyl 2-benzylpropanedioateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5202412-Benzylpropane-1,3-diol

Procedure

Diethyl benzylmalonate is reduced with lithium aluminium hydride to give 2-benzylpropane-1,3-diol (m.p. 64°-65° C.) and esterified with an equimolar amount of benzenesulphochloride in anhydrous pyridine to give 2-benzylpropane-1,3-diol monobenzenesulphonate (oily substance). Reaction thereof with the sodium salt of hexadecanethiol in ethanol gives the desired 2-benzyl-3-hexadecylthiopropan-1-ol (wax-like compound).

Sources & evidence

ORD record
ord-0f17ab36f84d430d98f31d28553808f7
Source dataset
uspto-grants-1984_04
Patent number
US04444766

Linked notes

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