2,4-Dihydroxybenzaldehyde → 2,4-Bis(benzyloxy)benzaldehyde

HRID 981379Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 72132,4-Dihydroxybenzaldehyde

HCID 7503Benzyl Chloride

Product 1

HCID 18090802,4-Bis(benzyloxy)benzaldehyde

Procedure

That is, 2,4-dihydroxybenzaldehyde [IV] is benzylated with benzyl chloride to produce 2,4-dibenzyloxybenzaldehyde [V], then [V] is reduced with sodium borohydride to produce 2,4-dibenzyloxybenzyl alcohol [VI] and then, [VI] is chlorinated with thionyl chloride to produce 2,4-dibenzyloxybenzyl chloride [VII]. Then, [VII] is allowed to react with sodium cyanide to obtain 2,4-dibenzyloxyphenyl acetonitrile [VIII], thereafter [VIII] is hydrolyzed with an alkali to produce 2,4-dibenzyloxyphenylacetic acid [IX], then this [IX] is chlorinated with thionyl chloride to produce 2,4-dibenzyloxyphenylacetyl chloride [X] and further, this [X] is allowed to react with L-asparagine or glutamine p-nitrophenyl ester to obtain [IIa].

Sources & evidence

ORD record: ord-5cf54842162b4b649d389fd9ab218675
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04990614

Reaction notes

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