3-Hydroxybenzaldehyde → HCID 10753946, compound
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][CH:21]=1)[CH:17]=[O:18]>>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18]Participants
3
Procedure
2-Bromomethylnaphthalene was reacted with 3-hydroxybenzaldehyde using the procedure described in Example 1 to give 3-(naphth-2-ylmethoxy)benzaldehyde in 93% yield, m.p. 108°-110° C. (recrystallised from ethanol). The product so obtained was reacted with thiazol-2-yl-lithium using the procedure described in the 4th paragraph of the portion of Example 1 which is concerned with the preparation of starting materials except that the product was purified by column chromatography using a 1:1 v/v mixture of petroleum ether (b.p. 60°-80° C.) and diethyl ether as eluent. There was thus obtained the required starting material in 62% yield, m.p. 105°-106° C.
Sources & evidence
- ORD record
- ord-1f428deae4dc4c979d0bc2b3901d8831
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05196422
Reaction notes
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