Ethanol → Ethyl phenylacetate

HRID 1439799Notes

Reaction equation

HRID 1439799 reaction equation
[CH2:1]([Cl:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][CH2:10][O-:11].[Na+].O.[O-:14]S(S([O-])=O)=O.[Na+].[Na+].[CH2:22]([OH:24])[CH3:23]>[Mn]>[CH2:1]([Cl:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([O:11][C:22](=[O:24])[CH2:23][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9].[C:2]1([CH2:1][C:10]([OH:11])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([O:11][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

10

Reactant 5

HCID 702EthanolHCID 962WaterHCID 7503Benzyl ChlorideHCID 24489Sodium DithioniteHCID 2723922Sodium ethoxide

Product 4

HCID 999Phenylacetic AcidYield 6%HCID 7503Benzyl ChlorideHCID 7590Ethyl phenylacetateYield 71%HCID 10873Benzyl ethyl ether

Reagents, catalysts & solvents 1

HCID 23930ManganeseCatalyst

Procedure

In a manner similar to Example 17, 126.5 g of benzyl chloride, 794 g of a 9 wt-% solution of sodium ethylate in ethanol, 12 g CoCl2.6 H2O, 6 g manganese powder and 1 g Na2S2O4 were reacted with CO. After the usual processing, 8 g of benzyl chloride, 109 g of phenylacetic acid ethyl ester (yield 71%), 8 g of phenylacetic acid (yield 6%) and 1 g of ethylbenzyl ether were isolated.

Sources & evidence

ORD record
ord-eed0a59619294e98b29d2342243aea32
Source dataset
uspto-grants-1977_11
Patent number
US04060690

Reaction notes

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