Morpholine → (4-Hydroxy-3,5-dimethylphenyl)acetic acid

HRID 2248424Notes

Reaction equation

C([C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=1)(=O)C.[S].N1[CH2:19][CH2:18][O:17]CC1.[OH:20]CC[NH-]>>[OH:11][C:7]1[C:8]([CH3:10])=[CH:9][C:4]([CH2:19][C:18]([OH:17])=[O:20])=[CH:5][C:6]=1[CH3:12]

Participants

Reactant 4

HCID 8083Morpholine

HCID 365814'-Hydroxy-3',5'-dimethylacetophenone

HCID 5362487Sulfur

HCID 867336622-Hydroxyethylamide

Product 1

HCID 16767514(4-Hydroxy-3,5-dimethylphenyl)acetic acid

Procedure

2-(4-Hydroxy-3,5-dimethylphenyl)acetic acid is prepared in a known way (cf. J. Org. Chem. 11, 798 (1946)) from 4-acetyl-2,6-dimethylphenol, sulfur, and morpholine (Willgeroth-Kindler Reaction) and has a melting point of 147° C. The acid is converted into the 2-hydroxyethylamide (yellow-brown oil) through the methyl ester (melting point 95° C.) by the method of Example 1.1.

Sources & evidence

ORD record: ord-3c8dd07750914882917d110df1e42932
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05039781

Reaction notes

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