Hydrochloric Acid → 2-(Benzyloxymethyl)-4,6-dihydroxybenzoic acid methyl ester

HRID 505664Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:27])[C:4]1[C:9]([O:10]COC)=[CH:8][C:7]([O:14]COC)=[CH:6][C:5]=1[CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>C(O)C>[CH3:1][O:2][C:3](=[O:27])[C:4]1[C:9]([OH:10])=[CH:8][C:7]([OH:14])=[CH:6][C:5]=1[CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The above-obtained 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid methyl ester (10 mg, 0.027 mmol) was dissolved in ethanol (4 mL) and the obtained solution was added with concentrated hydrochloric acid (0.10 mL) and stirred at 60° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to obtain Compound 22 (12 mg, 100%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record: ord-fbb95fd102294e3f97e8ef5a695b6d09
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781485B2

Reaction notes

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