Hydrochloric Acid → (2-(Benzyloxy)-3-methoxyphenyl)methanol

HRID 982111Notes

Reaction equation

[BH4-].[Na+].[CH2:3]([O:10][C:11]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.Cl>C(O)C.C(OCC)C>[CH2:3]([O:10][C:11]1[C:12]([CH2:13][OH:14])=[CH:15][CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a well-stirred suspension of 2.0 g (52.7 mmol) of sodium borohydride in 65 mL of ethyl alcohol at 0° C. under a nitrogen atmosphere, was slowly added 15 g (61.9 mmol) of 2-benzyloxy-3-methoxybenzaldehyde, from Step 1, in 100 mL of ethyl alcohol. The reaction mixture was stirred at 0° C. for 10 minutes and then 50 mL of water was added to quench the reaction, followed by 50 mL of diethyl ether. The mixture was slowly added to 60 mL of 10% aqueous hydrochloric acid solution at 0° C. and the resultant mixture was stirred for 1 h and then extracted with 3×200 mL of diethyl ether. The combined ether extracts were washed with aqueous sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 15.14 g (100% yield) of the title compound as a white solid.

Workup

customto quench
customthe reaction
extractionextracted with 3×200 mL of diethyl ether
washThe combined ether extracts were washed with aqueous sodium bicarbonate solution, water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-432a44b84df0486e9010cf99ccd65177
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994486

Reaction notes

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