Ethyl Thioglycolate → Ethyl (2,4,6-trimethylbenzylthio)acetate

HRID 1074095Notes

Reaction equation

HRID 1074095 reaction equation
CC1C=CC(C[S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=CC=1.[CH3:16][C:17]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:18]=1[CH2:19]Cl.CC[O-].[Na+].SCC(OCC)=O>C(O)C>[CH3:16][C:17]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:18]=1[CH2:19][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 12185Ethyl ThioglycolateHCID 741082,4,6-Trimethylbenzyl chlorideHCID 2723922Sodium ethoxideHCID 4107274Ethyl (4-methylbenzylthio)acetate

Product 1

HCID 13245053Ethyl (2,4,6-trimethylbenzylthio)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure is as in Example 29 for the preparation of ethyl (4-methylbenzylthio)acetate, starting with 2,4,6-trimethylbenzyl chloride (10.25 g), a 2M ethanolic solution of sodium ethylate (32.5 cc) and ethyl 2-mercaptoacetate (7.1 g) in ethanol (150 cc). Ethyl (2,4,6-trimethylbenzylthio)acetate (11 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-982536e5629c4561a114a12a1c47c86c
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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