Benzyl Alcohol → 2-(Benzyloxy)propanoic acid

Reaction equation

CCOCC.[Na].Cl[CH:8]([CH3:12])[C:9]([OH:11])=[O:10].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([O:20][CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 4

HCID 244Benzyl Alcohol2×

HCID 3283Diethyl Ether

HCID 117342-Chloropropionic acid

HCID 5360545Sodium2×

Product 1

HCID 2459872-(Benzyloxy)propanoic acid

Conditions

Temperature: 150 °C

Procedure

An alternate method for the preparation of ether compounds corresponding to Formula I (R=alkyl, phenylalkyl) follows. Sodium metal (about 12 g) was added cautiously to a stirred cold (ice bath) portion (250 mL) of benzyl alcohol. After most of the sodium metal had dissolved, the reaction was heated to 150° C. 2-Chloropropionic acid (27.2 g, 0.25 mole) was added dropwise in 35 mL of benzyl alcohol and the resulting mixture heated on additional 3 hours. Concentration in vacuo gave crude 2-benzyloxypropionic acid which was used without further purification.