6-[(Triphenylmethyl)thio]-1,3,3-hexanetricarboxylic acid → 2-(3-tritylsulfanylpropyl)pentanedioic Acid

HRID 1386875Notes

Reaction equation

[C:1]1([C:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:8][CH2:9][CH2:10][CH2:11][C:12](C(O)=O)([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CS(C)=O>[C:30]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[S:8][CH2:9][CH2:10][CH2:11][CH:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2.56 mmol of 6-[(triphenylmethyl)thio]-1,3,3,-hexanetricarboxylic acid (III) (1.36 g) was dissolved in 5 ml of dimethylsulfoxide and the solution was heated to 100° C. for 1 hour, evaporated to dryness, dissolved in water and precipitated by addition of 1 M sulfuric acid. The precipitated oil solidified after 1 hour treatment in an ultrasound bath. The solid was filtered off, washed with water and dried in a dessicator. Yield 1.1 g of 6-[(triphenylmethyl)thio]-1,3-hexanedicarboxylic acid (IV) (89% two steps from II), 13C-NMR (MeOH) δ 27.9, 28.6, 33.0 (two carbons), 33.1, 45.9, 68.1, 128.1, 129.2, 131.2, 146.8, 177.1, 179.4.

Workup

customevaporated to dryness
dissolutiondissolved in water
customprecipitated by addition of 1 M sulfuric acid
filtrationThe solid was filtered off
washwashed with water
customdried in a dessicator

Sources & evidence

ORD record: ord-5426a12f0c5041249308278e74a90b5f
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265609B1

Reaction notes

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