Water → HCID 89601252, compound

HRID 523347Notes

Reaction equation

HRID 523347 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][CH:8]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][CH:9]1[CH2:15][OH:16].[OH2:17]>N1C=CC=CC=1>[CH3:7][CH:8]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][CH:9]1[CH2:15][O:16][C:1](=[O:5])[C:2]([O:17][CH2:15][CH:9]1[CH2:10][CH2:11][C:12]([CH3:14])=[CH:13][CH:8]1[CH3:7])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 106743(2,4-Dimethyl-3-cyclohexen-1-yl)methanol

Product 1

HCID 89601252HCID 89601252, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Oxalyl chloride (10 ml, 116 mmol) was added dropwise to a stirred solution of (±)-(2,4-dimethylcyclohex-3-en-1-yl)methanol (32.48 g, 233 mmol, cis/trans ca. 4:1) in pyridine (270 ml) at 0° C. over a period of 15 min. The solution was allowed to warm up to room temperature and, after 21 h, was poured onto cold water, extracted with diethyl ether (2×), H2SO4 (10%) (2×), NaHCO3 (sat.) and NaCl (sat.). The organic layer was dried (Na2SO4) and concentrated. Column chromatography (SiO2, heptane/ether 8:2) gave 32.85 g (85%) of (±)-bis[(2,4-dimethyl-3-cyclohexen-1-yl)methyl]oxalate as a slightly yellow oil (mixture of cis/trans-isomers ca. 4:1).

Workup

  1. extractionextracted with diethyl ether (2×), H2SO4 (10%) (2×), NaHCO3 (sat.) and NaCl (sat.)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7e681c9611ff479a980c509d74384934
Source dataset
uspto-grants-2016_05
Patent number
US09334464B2

Reaction notes

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