4-Hydroxybenzaldehyde → HCID 58284274, compound

HRID 714442Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH2:11][C:12]([CH3:15])([OH:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[OH:14][C:12]([CH3:15])([CH3:13])[CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

5 g (40.94 mmol) of 4-hydroxybenzaldehyde were initially charged in 50 ml of DMF. 4.45 g (40.94 mmol) of 1-chloro-2-methylpropan-2-ol and 6.08 g (57.32 mmol) of sodium carbonate were added, and the mixture was then stirred at 130° C. overnight. Saturated aqueous sodium bicarbonate solution/ethyl acetate were added to the reaction mixture. The precipitate was filtered off and discarded. The two phases were separated from one another, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated using a rotary evaporator. The residue was purified by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5/1→1/2).

Workup

filtrationThe precipitate was filtered off
customThe two phases were separated from one another, and the aqueous phase
extractionwas extracted three times with ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customa rotary evaporator
customThe residue was purified by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5/1→1/2)

Sources & evidence

ORD record: ord-d690bf7bb4334bf6a778486749409e2d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187428B2

Reaction notes

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