Guaiacol → HCID 18537920, compound

HRID 412713Notes

Reaction equation

HRID 412713 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 18537920HCID 18537920, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methoxyphenol (9.8 mL, 89.3 mmol), dimethylformamide (100 mL) and potassium carbonate (61.5 g, 445 mmol) was stirred at 23° C. while as tert-butyl 2-bromoethylcarbamate (20 g, 89.3 mmol) was added. The mixture was stirred for 24 hours and then poured into ethyl ether:hexanes (1:1, 400 mL) and was washed with water (5×50 mL). The aqueous layer was extracted with ethyl ether:hexanes (1:1, 3×40 mL) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo to provide tert-butyl 2-(2-methoxyphenoxy)ethylcarbamate (23.22 g, 97% yield) as a yellow oil; MS (PB-PCI) C14H21NO4 m/e calc 267.32; found 268 (MH+).

Workup

  1. additionwas added
  2. washwas washed with water (5×50 mL)
  3. extractionThe aqueous layer was extracted with ethyl ether:hexanes (1:1, 3×40 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce43db629aa047c79ef3632700d9d479
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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