Acetic Acid → HCID 22761101, compound

HRID 1704122Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.CS(O[CH:20]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH3:21])(=O)=O.C(O)(=O)C>CN(C)C(=O)C>[CH3:14][O:13][C:11](=[O:12])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH:20]([CH3:21])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 8.0 g of sodium hydride (60% dispersion in oil) (washed with hexane) in 190 ml of N,N-dimethylacetamide is added dropwise 35.2 g of methyl p-hydroxyphenylacetate in 60 ml of N,N-dimethylacetamide. The mixture is stirred at room temperature for one hour and at 50° C. for 20 minutes. To the mixture is added dropwise 53 g of 3-(p-chlorophenoxy)propan-2-ol O-methanesulfonate in 100 ml of N,N-dimethylacetamide. The mixture is stirred and heated at 100° C. for 18 hours. After pouring into 2 liters of ice-water containing 6 ml of acetic acid and chilling in an ice bath for 2 hours, the mixture is filtered and the solid washed with water. The damp waxy product is dissolved in dichloromethane and the solution dried (MgSO4). The solvent is removed under reduced pressure to give 52.6 g of product as an oil. The oil is crystallized from hexane and recrystallized from methanol to give the product as white crystals, mp 84°- 85° C.

Workup

stirringThe mixture is stirred
temperatureheated at 100° C. for 18 hours
temperaturechilling in an ice bath for 2 hours
filtrationthe mixture is filtered
washthe solid washed with water
dissolutionThe damp waxy product is dissolved in dichloromethane
dry with materialthe solution dried (MgSO4)
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-52a95e81d07e496db6b13c5e929a7f93
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04125732

Reaction notes

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