Phthalaldehyde → 1,3-Benzenedimethanol

HRID 1019354Notes

Reaction equation

HRID 1019354 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].C(=O)C1C(=CC=CC=1)[CH:14]=[O:15].OC[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH:25]=[O:26]>>[C:5]1([CH2:4][OH:3])[CH:6]=[CH:7][CH:8]=[C:9]([CH2:14][OH:15])[CH:10]=1.[OH:2][CH2:1][C:28]1[CH:27]=[C:24]([CH:23]=[CH:30][CH:29]=1)[CH:25]=[O:26]

Participants

5

Reactant 3

HCID 4807PhthalaldehydeHCID 6885PhthalideHCID 184728Benzaldehyde, hydroxymethyl-

Product 2

HCID 693741,3-BenzenedimethanolHCID 131314553-(Hydroxymethyl)benzaldehyde

Procedure

A particularly advantageous feature of the oxidative method is shape selectivity, as illustrated by the oxidation of three benzenedimethanol isomers as shown in FIG. 1 (Example 6 below). Oxidation of 1,2-benzenedimethanol resulted in very low conversion, yielding a mixture of phthalide, phthalaldehyde, and 2-(hydroxymethyl)benzaldehyde (a mono-oxidized product). Oxidation of 1,3-benzenedimethanol yielded only the mono-oxidized product 3-(hydroxymethyl)benzaldehyde. Oxidation of 1,4-benzenedimethanol yielded terephthalaldehyde. These results show that the H-K-OMS-2 catalyst gives shape selective reaction products.

Workup

  1. customyielding

Sources & evidence

ORD record
ord-b5abf0be392c4f0eab5bf51cc2624939
Source dataset
uspto-grants-2002_11
Patent number
US06486357B2

Reaction notes

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