Butyric acid, p-methoxyphenyl ester → HCID 15160988, compound

HRID 1535058Notes

Reaction equation

HRID 1535058 reaction equation
C([O:6][C:7]1[CH:12]=CC(OC)=[CH:9][C:8]=1[CH:15](C)C(C)=C)(=O)CCC.[C:20]([O:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:24])[CH2:21][CH2:22][CH3:23].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Ca+2].[OH-]>ClCCl>[C:20]([O:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][C:31]=1[C:8]([CH3:15])([CH3:9])[CH:7]1[O:6][CH2:12]1)(=[O:24])[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 26766Butyric acid, p-methoxyphenyl esterHCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 15160987HCID 15160987, compound

Product 1

HCID 15160988HCID 15160988, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of E61, o-(1,2-dimethylallyl)-p-methoxyphenyl n-butyrate and p-methoxyphenyl n-butyrate (39.5 gm) in dichloromethane (900 mL) was added in portions metachloroperbenzoic acid (52 gm; 300 mmoles). The mixture was stirred at room temperature overnight. The reaction mixture was cooled in an ice-water bath and calcium hydroxide (150 gm) was added. After stirring for 15 minutes the mixture was filtered through a celite pad and the filtrate concentrated in vacuo. The residue was chromatographed in silica gel using 10% ethyl acetate in hexane to obtain 20 gm (47%) of o-(1,1-dimethyl-2,3-epoxypropyl)-p-methoxyphenyl n-butyrate, E62, as an oil.

Workup

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. stirringAfter stirring for 15 minutes the mixture
  3. filtrationwas filtered through a celite pad
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was chromatographed in silica gel using 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e478b62f8b4b46fcb4b06dcaf4e48134
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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