Ethylene Glycol → 2-({[4-(1,1-Dimethylethyl)phenyl]methyl}oxy)ethanol

HRID 2283113Notes

Reaction equation

[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1.O>C1COCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(C)=O>[CH3:18][C:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][O:3][CH2:2][CH2:1][OH:4])=[CH:14][CH:13]=1)([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL). 1-(Bromomethyl)-4-(1,1-dimethylethyl)benzene (0.28 mL, 1.5 mmol) was added to the reaction, and the residual 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) was then added, and the reaction was heated at 60° C. for 18 h and then rt for 4 h. H2O (2 mL) and EtOAc (2 mL) were added, and the layers were separated via pipette. The aqueous layer was extracted with EtOAc (1×1 mL), and the combined organic layers were concentrated. The crude product was purified on a SPE cartridge (5 g silica) eluting with the following 10 mL fractions: 10% EtOAc/hexanes (fractions 1,2), 30% EtOAc/hexanes (fractions 3,4), and 50% EtOAc/hexanes (fractions 5,6) to give the title compound (312 mg, 51%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

Workup

customthe layers were separated via pipette
extractionThe aqueous layer was extracted with EtOAc (1×1 mL)
concentrationthe combined organic layers were concentrated
customThe crude product was purified on a SPE cartridge (5 g silica)
washeluting with the following 10 mL fractions

Sources & evidence

ORD record: ord-c372aa02446c421e8758644b13468c7a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09144571B2

Reaction notes

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