2,3-Dihydroxybutanedioic Acid → Butanedioic acid, 2,3-dihydroxy-, didodecyl ester

HRID 1439834Notes

Reaction equation

[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:14]([OH:23])(=[O:22])[CH:15]([CH:17]([C:19]([OH:21])=O)[OH:18])[OH:16].[C:24]1([CH3:34])[CH:29]=[CH:28][C:27](S(O)(=O)=O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[C:14]([O:23][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:24][CH3:34])(=[O:22])[CH:15]([CH:17]([C:19]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:21])[OH:18])[OH:16]

Participants

Conditions

Temperature: 150 °C

Procedure

In a 2 l three-necked flask equipped with a condenser and a stirring device, 372.7 g (2 mol) of dodecanol, 150.1 g (1 mol) of tartaric acid, 500 ml of toluene and 17.2 g (0.1 mol) of p-toluenesulfonic acid were placed, heated to 150° C. and reacted for 12 hours as azeotropic dehydration was run under refluxing toluene. The reaction solution was cooled to room temperature, and the toluene was distilled away under reduced pressure. The thus obtained oily material was submitted to chromatographic separation and purification on a column of silica gel (eluent: ethylacetate/hexane=1/1) to give 377.7 g of the intended compound as a colorless transparent liquid (yield: 77.6%).

Workup

customIn a 2 l three-necked flask equipped with a condenser
customreacted for 12 hours as azeotropic dehydration
temperatureThe reaction solution was cooled to room temperature
distillationthe toluene was distilled away under reduced pressure
customThe thus obtained oily material was submitted to chromatographic separation and purification on a column of silica gel (eluent: ethylacetate/hexane=1/1)

Sources & evidence

ORD record: ord-8934ce9b3b10499eb3b50af78b8135df
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496681

Reaction notes

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