Iodoethane → Acetic acid, (ethylthio)-, ethyl ester

HRID 1074083Notes

Reaction equation

HRID 1074083 reaction equation
CC1C=C[C:5]([CH2:6][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=CC=1.ICC.CC[O-].[Na+].SCC(OCC)=O>C(O)C>[CH2:6]([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:5]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 4107274Ethyl (4-methylbenzylthio)acetate

Product 1

HCID 350365Acetic acid, (ethylthio)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure is as in Example 29 for the preparation of ethyl (4-methylbenzylthio)acetate, starting with iodoethane (10.5 g), a 2M ethanolic solution of sodium ethylate (37 cc) and ethyl 2-mercaptoacetate (8.1 g) in ethanol (100 cc). Ethyl (ethylthio)acetate (6.9 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-60ac2388cb32472eb2e5f32e02366b23
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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