Dimethylformamide → 3-(4-Tetradecylphenoxy)-1,2-propanediol

HRID 235717

Reaction equation

[CH2:1]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Na+].[O:24]1[CH2:28][CH2:27][O:26]C1.[CH3:29]N(C)C=O>CCCCCC.CCOCC>[CH2:1]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:29][CH:28]([OH:24])[CH2:27][OH:26])=[CH:19][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

An about 43.5 g portion of 4-tetradecyl phenol was added in portions to a suspension of about 10.8 g of prewashed sodium hydride in dimethylformamide. The mixture was refluxed about 11/2 hours, allowed to cool and about 37.8 g of 2,2-dimethyl-4-[[methylsulfonyl)oxy]methyl]-1,3-dioxolane was added. This mixture was heated to about 80° C. for about 24 hours; diluted with hexane and ether, washed with water and brine and evaporated. The residue was heated on a steam bath with about 500 ml of methanol and about 80 ml of dilute hydrochloric acid for one hour, cooled, partially evaporated, the solid collected and recrystallized from methanol, giving about 38 g of the desired title compound, mp 81.5°-83.5° C.

Workup

temperatureThe mixture was refluxed about 11/2 hours
temperatureto cool
washwashed with water and brine
customevaporated
temperatureThe residue was heated on a steam bath with about 500 ml of methanol and about 80 ml of dilute hydrochloric acid for one hour
temperaturecooled
custompartially evaporated
customthe solid collected
customrecrystallized from methanol

Sources & evidence

ORD record: ord-65c54c27b3da49ca840c4785aa94538a
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640913

Linked notes

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