Morpholine → 2,3-Dimethoxy-5-methyl-6-[(morpholin-4-yl)methyl]benzene-1,4-diol

HRID 2351938Notes

Reaction equation

HRID 2351938 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([O:9][CH3:10])[C:5]([O:11][CH3:12])=[C:4]([OH:13])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.O1CCOC[CH2:21]1>>[CH3:12][O:11][C:5]1[C:6]([O:9][CH3:10])=[C:7]([OH:8])[C:2]([CH3:1])=[C:3]([CH2:21][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:4]=1[OH:13]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 312751,4-DioxaneHCID 111830272,3-Dimethoxy-5-methyl-1,4-benzenediol

Product 1

HCID 135185542,3-Dimethoxy-5-methyl-6-[(morpholin-4-yl)methyl]benzene-1,4-diol

Procedure

A solution of 2,3-dimethoxy-5-methyl-1,4-benzohydroquinone (2.2 g) 37% formaldehyde (2.4 ml) and morpholine (2.4 ml) in dioxane (11 ml) was refluxed at 100° C. for 2 hours. The reaction mixture was evaporated to dryness and the residue was suspended in water. The suspension was extracted with chloroform and the extract was treated in a conventional manner. The residue was recrystallized from ether-hexane to give 2,3-dimethoxy-5-methyl-6-morpholinomethylhydroquinone (2.23 g), melting at 127°-130° C.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionThe suspension was extracted with chloroform
  3. additionthe extract was treated in a conventional manner
  4. customThe residue was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-4afc5690d32745c78d1488e110e0bb3f
Source dataset
uspto-grants-1989_10
Patent number
US04874752

Reaction notes

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