Ethylene Oxide → N-[2-(2-Hydroxyethyl)-3-methoxyphenyl]-2,2-dimethylpropanamide

HRID 1577152Notes

Reaction equation

[C:1]([NH:7][C:8]1[CH:15]=[CH:14][C:11](OC)=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1C[O:19][CH2:18][CH2:17]1.C([Li])CCC.C1[O:28][CH2:27]1>CCCCCC.O.C(O)(=O)C>[OH:19][CH2:18][CH2:17][C:9]1[C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5])=[CH:15][CH:14]=[CH:11][C:10]=1[O:28][CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To N-pivaloylanisidine (4.14 g, 0.02 mole) in freshly distilled THF (60 ml) under nitrogen is added 2.3 N butyllithium in hexane (23 ml) at 0° C. and the resultant solution is stirred at 0° C. for 2 hours. Ethylene oxide (liquid, 1.6 ml) is added and the reaction mixture is stirred for an hour at 0° C. and then an additional hour at ambient temperature. Acetic acid (2 ml) and water (30 ml) are added to quench the reaction. The THF is evaporated in vacuo and the aqueous mixture is extracted with ether (2×30 ml). The extracts are combined, washed with 5% sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated to 5.42 g of crystalline material. Recrystallization from n-butyl chloride (13 ml) gives 3.46 g (69%) of 2-(2-hydroxyethyl)-3-pivalamidoanisole, m.p. 118°-119.5° C.

Workup

customat ambient temperature
customto quench
customthe reaction
customThe THF is evaporated in vacuo
extractionthe aqueous mixture is extracted with ether (2×30 ml)
washwashed with 5% sodium bicarbonate solution, brine
dry with materialdried over sodium sulfate
concentrationconcentrated to 5.42 g of crystalline material
customRecrystallization from n-butyl chloride (13 ml)

Sources & evidence

ORD record: ord-5dd1f8aa5149401a90f906e6d21522dd
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04287201

Reaction notes

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