Ethyl Thioglycolate → Ethyl (4-isopropylbenzylthio)acetate

HRID 477357

Reaction equation

HRID 477357 reaction equation
CC1C=CC(C[S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=CC=1.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=1.CC[O-].[Na+].SCC(OCC)=O>C(O)C>[CH:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:17][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:19][CH:20]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 12185Ethyl ThioglycolateHCID 477191-(Bromomethyl)-4-(propan-2-yl)benzeneHCID 2723922Sodium ethoxideHCID 4107274Ethyl (4-methylbenzylthio)acetate

Product 1

HCID 54329641Ethyl (4-isopropylbenzylthio)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 1-bromomethyl-4-isopropylbenzene (15 g), a 2M ethanolic solution of sodium ethylate (49 cc) and ethyl 2-mercaptoacetate (9.8 g) in ethanol (150 cc). Ethyl (4-isopropylbenzylthio)acetate (17.9 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-167924ff349a43748a60649d422b4d13
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

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