Toluene → 2-(N,N-diethylcarbamoyloxy)-6-methoxytoluene

HRID 1640070Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([N:19]([CH2:23][CH3:24])[C:20](Cl)=[O:21])[CH3:18].C1(C)C=CC=CC=1>C(#N)C.O>[CH2:17]([N:19]([CH2:23][CH3:24])[C:20]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH3:10])=[O:21])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 3.15 g (22.8 mmol) of 2-hydroxy-6-methoxytoluene in 16 mL acetonitrile was added with 3.50 g (25.1 mmol) of potassium carbonate and 3.4 g (25.1 mmol) of diethylcarbamoyl chloride and heated and stirred on a 100° C. oil bath for 59 minutes. After addition of 0.6 g (4.4 mmol) of diethylcarbamoyl chloride and heated for 38 minutes, while stirring on an ice-water bath, 30 mL of toluene and 30 mL of water, were added into the reaction mixture, and the mixture was stirred for 20 minutes, transferred to a separatory funnel and settled. The aqueous layer was separated and discarded and after the organic layer was washed with 10 mL of 2 N aqueous sodium hydroxide and 10 mL of water twice, and the solvent was evaporated to obtain 5.58 g of the crude title compound. Since the mixture solidified, a part thereof was obtained as seed crystals.

Workup

temperatureheated
temperatureheated for 38 minutes
stirringwhile stirring on an ice-water bath
stirringthe mixture was stirred for 20 minutes
customtransferred to a separatory funnel
customThe aqueous layer was separated
washafter the organic layer was washed with 10 mL of 2 N aqueous sodium hydroxide and 10 mL of water twice
customthe solvent was evaporated

Sources & evidence

ORD record: ord-5950d7e3dc2543a7a7efd261dad2d13c
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110688B2

Reaction notes

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