Isovanillin → HCID 19773026, compound

HRID 1614238Notes

Reaction equation

Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[OH:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:17]=[O:18]>>[CH3:23][O:22][C:21]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[O:13][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

Participants

Reactant 2

HCID 12127Isovanillin

HCID 703202-Bromomethylnaphthalene

Product 1

HCID 19773026HCID 19773026, compoundYield 50%

Procedure

2-Bromomethylnaphthalene was reacted with 3-hydroxy-4-methoxybenzaldehyde using the conditions described in Example 1 to give 4-methoxy-3-(naphth-2-ylmethoxy)benzaldehyde in 50% yield, m.p. 80° C. Following the procedure described in Note k. above the product so obtained was reacted with thiazol-2-yl-lithium to give 2-[4-methoxy-3-(naphth-2-ylmethoxy)-α-hydroxybenzyl]thiazole as an oil in 62% yield; that product was oxidised with sodium dichromate to give 4-methoxy-3-(naphth-2-ylmethoxy)phenyl 2-thiazolyl ketone in 58% yield, m.p. 149°-150° C.; and the product so obtained was reacted with ethylmagnesium iodide to give the required starting material in 45% yield, m.p. 80° C.

Sources & evidence

ORD record: ord-73611670e6c8473488c9bfcd2e02fbc3
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196422

Reaction notes

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