Diethyl phenylmalonate → 2-Phenyl-1,3-propanediol

HRID 326110

Reaction equation

[C:1]1([CH:7]([C:13](OCC)=[O:14])[C:8](OCC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:1]1([CH:7]([CH2:8][OH:9])[CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 66514Diethyl phenylmalonate

HCID 21226445Aluminium lithium hydride

Product 1

HCID 2541782-Phenyl-1,3-propanediol

Procedure

Diethyl phenylmalonate is reduced with lithium aluminium hydride to give 2-phenyl-propane-1,3-diol and esterified with an equimolar amount of benzenesulphochloride in anhydrous pyridine to give 2-phenylpropane-1,3-diol monobenzenesulphonate (wax-like substance). Reaction thereof with the potassium salt of hexadecanethiol in ethanol gives the desired 3-hexadecylthio-2-phenylpropan-1-ol (wax-like substance).

Sources & evidence

ORD record: ord-7f5d1e8ecac34e5992d55dd88c945cb7
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04444766

Linked notes

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