Sodium Hydroxide → 6-[(Triphenylmethyl)thio]-1,3,3-hexanetricarboxylic acid

HRID 842599Notes

Reaction equation

C[O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1([CH2:16][CH2:17][CH2:18][S:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11](=[O:12])[O:10]C(C)(C)[O:8][C:7]1=[O:15].[OH-].[Na+]>O1CCOCC1.O>[C:27]1([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:19][CH2:18][CH2:17][CH2:16][C:6]([C:11]([OH:12])=[O:10])([C:7]([OH:15])=[O:8])[CH2:5][CH2:4][C:3]([OH:39])=[O:2])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2.56 mmol of 2,2-dimethyl-4,6-dioxo-5-[3-[(triphenylmethyl)thio]propyl]-1,3-dioxane-5-propanoic acid methyl ester (II) (1.4 g) with 18 mmol of sodium hydroxide (0.72 g) was dissolved in a mixture of 5 ml of 1,4-dioxane and 5 ml of water. The mixture was then heated to 100° C. for 1 hour, evaporated to dryness, dissolved in water and precipitated by addition of 1 M sulfuric acid. The precipitate was filtered off, washed with water and dried in a dessicator. Yield 1.36 g of 6-[(triphenylmethyl)thio]-1,3,3-hexanetricarboxylic acid (III) (−100%), 13C-NMR (MeOH) δ25.4, 29.2, 30.7, 33.5, 33.7, 58.0, 68.3, 128.1, 129.3, 131.2, 146.7, 174.9, 176.9.

Workup

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

Sources & evidence

ORD record: ord-e688f868d8e04c2e82a29c9f1bba5088
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376478B1

Reaction notes

Loading…