Dimethyl Sulfoxide → HCID 88537164, compound

HRID 2280235Notes

Reaction equation

HRID 2280235 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.O[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].Cl.[NH2:25][OH:26].[OH-].[Na+]>ClCCl>[OH:26]/[N:25]=[C:20](\[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])/[C:21]([OH:23])=[O:22]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 7430010-Hydroxydecanoic AcidHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 88537164HCID 88537164, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethyl sulfoxide (1.17 g, 15 mmol) in dichloromethane (50 mL) is cooled to −30° C. and treated with oxalyl chloride (1.92 g, 15 mmol). The reaction mixture is then treated with 10-hydroxydecanoic acid (2.06 g, 10 mmol) in dichloromethane (50 mL) and allowed to warm to room temperature over a period of 2 h. The reaction is then washed with water (2×50 mL). The organic layer is dried over sodium sulfate and then treated with hydroxylamine hydrochloride (1.03 g 15 mmol) and sodium hydroxide (0.6 g in 10 mL water) and stirred vigorously for 1 h. The organic phase is then separated dried over sodium sulfate and concentrated in vacuo to give 11[(E)-hydroxyimino-decanoic acid (1.8 g, 9.0 mmol).

Workup

  1. washThe reaction is then washed with water (2×50 mL)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customThe organic phase is then separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b32856ed2a3145bb8af076f166a1d22a
Source dataset
uspto-grants-2015_09
Patent number
US09138493B2

Reaction notes

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