Sulfuric Acid → HCID 53445966, compound

HRID 1107391Notes

Reaction equation

[CH:1]1(Br)C[CH2:4][CH2:3][CH2:2]1.[Mg].[C:8]1([C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S(=O)(=O)(O)[OH:22].CCO[CH2:29][CH3:30]>>[CH:30]1([C:9]2([OH:22])[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:29][CH2:4][CH2:3][CH2:2][CH2:1]1

Participants

Reactant 5

HCID 1118Sulfuric Acid

HCID 3283Diethyl Ether2×

HCID 8728Bromocyclopentane

HCID 15349Ethyl benzoylformate

HCID 5462224Magnesium

Product 1

HCID 53445966HCID 53445966, compoundYield 53.3%

Procedure

A solution of Grignard reagent prepared from cyclopentyl bromide (66 g) and magnesium (9 g) in absolute ether (240 ml) was added dropwise to a solution of ethyl phenylglyoxylate (30 g) in absolute ether (100 ml) at gently refluxing temperature. After the addition was completed, the reaction mixture was refluxed for 2 hours. The mixture was added to ice water (200 ml) and 10% diluted sulfuric acid (200 ml). The ether layer was separated from the reaction mixture, and then the aqueous layer was extracted with ether. The combined extracts were washed with water and dried over anhydrous sodium sulfate. The solvent was removed under pressure. The residue was vacuum distilled to obtain the title compound (23.5 g, 53.3%) as a pale yellow oil: bp 148 to 150° C. (6.5 mmHg).

Workup

temperatureat gently refluxing temperature
additionAfter the addition
temperaturethe reaction mixture was refluxed for 2 hours
customThe ether layer was separated from the reaction mixture
extractionthe aqueous layer was extracted with ether
washThe combined extracts were washed with water
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under pressure
distillationdistilled

Sources & evidence

ORD record: ord-984035ac92d046379bae2e429090ad58
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060485

Reaction notes

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