Lithium Hydroxide → 2,2-Bis-(2-phenylsulfanyl-ethyl)-malonic acid

HRID 1830124Notes

Reaction equation

C([O:3][C:4](=[O:29])[C:5]([CH2:20][CH2:21][S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:11][CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([O:8]CC)=[O:7])C.[OH-].[Li+]>C(O)C.O>[C:23]1([S:22][CH2:21][CH2:20][C:5]([CH2:11][CH2:12][S:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:4]([OH:29])=[O:3])[C:6]([OH:8])=[O:7])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 49 °C

Procedure

A solution of 2,2-bis-(2-phenylsulfanyl-ethyl)-malonic acid diethyl ester (5.614 g) in ethanol (100 mL) was treated with lithium hydroxide (2.84 g) in water (10 mL). The reaction mixture was heated at 49° C. for 17 hours followed by 85° C. for 2 hours. The solvents were evaporated at reduced pressure to give a residue that was treated with water (100 mL) and washed with ether. The aqueous layer was cooled on ice, acidified and the product extracted with ethyl acetate. The extracts were dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure to give acid 2,2-bis-(2-phenylsulfanyl-ethyl)-malonic acid (5.628 g).

Workup

customThe solvents were evaporated at reduced pressure
customto give a residue that
washwashed with ether
temperatureThe aqueous layer was cooled on ice
extractionthe product extracted with ethyl acetate
dry with materialThe extracts were dried over magnesium sulfate
customThe solvent was removed by rotary evaporation at reduced pressure

Sources & evidence

ORD record: ord-b0fded355c5b4af68af6197c8aea378b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064123B1

Reaction notes

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