3-Phenoxybenzyl chloride → Benzenemethanol, 3-phenoxy-, 1-acetate

HRID 1413579Notes

Reaction equation

HRID 1413579 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O-:19])(=[O:18])[CH3:17].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:16]([O:19][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 932913-Phenoxybenzyl chlorideHCID 517045Sodium Acetate

Product 1

HCID 170904Benzenemethanol, 3-phenoxy-, 1-acetateYield 99.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

m-Phenoxybenzyl chloride (218.5 g; 1 mole), sodium acetate (205 g; 2.5 mole), tetrabutylammonium bromide (10.9 g; 0.034 mole) and water (327 ml) were heated and stirred under reflux for 2 hours. On cooling m-Phenoxybenzyl acetate (241.5 g; 99.8% yield) separated as the upper layer. Its purity was 99%. m-Phenoxybenzyl acetate (242 g; 1 mole), sodium hydroxide (80 g; 2 mole), tetrabutylammonium bromide (12 g; 0.037 mole) and water (240 ml) were stirred at ambient temperature for 4 hours. The upper organic layer was dissolved in toluene (400 ml). The resulting solution was washed with water (2×200 ml) and treated with ion-exchange resin (Zerolit 236) and charcoal. Evaporation of the toluene gave the alcohol with a purity of 98.9% by gas chromatography (198 g, 99% yield).

Workup

  1. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-04d3457f65694c559b948685e3372b05
Source dataset
uspto-grants-1981_02
Patent number
US04250340

Reaction notes

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