3-Hydroxybenzaldehyde → HCID 19756597, compound

HRID 249374Notes

Reaction equation

HRID 249374 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].[OH:21][C:22]1C=C(C=CC=1)C=O.BrCC1C=CC2C(=CC=CC=2)C=1.C(=O)([O-])[O-].[K+].[K+].C(O[Mg]C[SiH](C)C)(C)C.[Cl-]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]([OH:17])[CH2:22][OH:21])[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 10753946HCID 10753946, compoundHCID 178459950HCID 178459950, compound

Product 1

HCID 19756597HCID 19756597, compound

Procedure

The appropriate alcohol starting material was obtained as follows: 3(Naphth-2-ylmethoxy)benzaldehyde [prepared by the alkylation of 3-hydroxybenzaldehyde with 2-bromomethylnaphthalene in the presence of potassium carbonate] was treated with isopropoxydimethysilylmethylmagnesium chloride using the procedure described in the portion of Example 1 which is concerned with the preparation of starting materials. After the oxidation step described therein there was obtained 2-[3-(naphth-2-ylmethoxy)phenyl]ethane-1,2-diol, m.p. 121°-122° C.

Workup

  1. customis concerned with the preparation of starting materials

Sources & evidence

ORD record
ord-3af684738f2143218e35c1ca90af8e2d
Source dataset
uspto-grants-1993_05
Patent number
US05214069

Reaction notes

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