Formaldehyde → 2-(Morpholin-4-ylmethyl)-5-ethylphenol

HRID 369444Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)[CH3:2].C=O.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[C:18]1(O)C=CC=CC=1>C(#N)C.N1CCOCC1>[N:12]1([CH2:18][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[OH:9])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 244.0 grams (1.78 moles--1.0 equiv.) of 89.1% pure m-ethylphenol in 320 mL (%Wt/Vol. Phenol to Solvent--76.3%) of acetonitrile was added 67.6 grams (2.14 moles--1.2 equiv.) of paraformaldehyde. Upon completion of addition, the mixture was stirred for ten minutes and then heated to 65° C. where 179.5 grams (2.06 moles--1.16 equiv.) of morpholine was added during a one hour period at a rate to maintain the reaction temperature below 70-75° C. Upon completion of addition, the reaction mixture was heated to 70° C. where it stirred for two hours. At this point, the reaction mixture was analyzed by GC, which indicated that 2% of the phenol starting material remained. An additional 3.5 grams (0.04 mole--0.02 equiv.) of morpholine was added. Upon completion addition, the reaction mixture was stirred at 70° C. until GC analysis indicated that 1.1% of the phenol starting material remained. The acetonitrile was removed under vacuum, yielding 446.6 grams of 89.1% pure 2-(morpholin-4-ylmethyl)-5-ethylphenol (90% yield).

Workup

additionUpon completion of addition
additionwas added during a one hour period at a rate
temperatureto maintain the reaction temperature below 70-75° C
additionUpon completion of addition
stirringstirred for two hours
additionUpon completion addition
stirringthe reaction mixture was stirred at 70° C. until GC analysis
customThe acetonitrile was removed under vacuum

Sources & evidence

ORD record: ord-e9dd78a4a53643acaaf9d0f153194cd0
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136972

Reaction notes

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