Reaction #2329034

Reaction equation

LAH

methyl 4-dodecyloxybenzoate

CH2Cl2

→

benzyl alcohol

Yield 88.0%

4-Dodecyloxybenzyl Alcohol

Yield 88.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONUpon addition
2. 2
   OtherReaction
3. 3
   Temperaturewas cooled to 0° C.
4. 4
   Otherquenched by successive addition of H2O (13 mL), 15% NaOH (13 mL), and H2O (39 mL)
5. 5
   workup.STIRRINGstirring
6. 6
   OtherReaction mixture
7. 7
   Filtrationwas then filtered
8. 8
   Washthe lithium salts rinsed generously with CH2Cl2
9. 9
   DryingThe filtrate was dried over MgSO4
10. 10
    Concentrationconcentrated

Procedure

To a 0° C. slurry of LAH (13.0 g, 343 mmol) in dry THF (400 mL) was added slowly methyl 4-dodecyloxybenzoate (100 g, 312 mmol) in dry THF (350 mL) over 1.5 hours. Upon addition, the mixture was stirred at room temperature for one hour, after which TLC (CH2Cl2) showed completion. Reaction was cooled to 0° C. and quenched by successive addition of H2O (13 mL), 15% NaOH (13 mL), and H2O (39 mL), and stirring continued until H2 evolution ceased. Reaction mixture was then filtered and the lithium salts rinsed generously with CH2Cl2. The filtrate was dried over MgSO4 and concentrated to give the title benzyl alcohol (80 g, 88%), which was taken to the next step without further purification.

Source