Process for the preparation of hydroquinones
AssigneeMerck Patent GmbH
InventorsShahuraj Hanamantrao Kadam, Shashikumar Paknikar
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Abstract
The invention relates to a process for the preparation of a hydroquinone compound of formula (I) wherein R2, R3, R5 and R6 have the meaning according to claim 1, with the steps of formylating a substituted phenol and oxidising the resulting substituted 4-hydroxy-benzaldehyde under acidic conditions to the corresponding hydroquinone of formula (I). Another object of the invention concerns the intermediate 2,3,5-trimethyl-4-hydroxy-benzaldehyde for synthesis of 2,3,5-trimethyl-hydroquinone (TMHQ) and (dl)α-tocopherol.
Claims16
A process for the preparation of a hydroquinone compound of formula (I)
- wherein
- R2, R3, R5, R6 is independently from one another H, A, Cyc, Hal, CN, —(CYY)n—OA, —(CYY)n—NYY, —O(CYY)n—OA, —O(CYY)n—NYY, —NH(CYY)n—OA or —NH(CYY)n—NYY;
- Y is H, A or Hal;
- A is unbranched or branched alkyl having 1-10 C atoms, in which 1-7 H atoms can be replaced by Hal, or in which one or two adjacent CH2 groups can be replaced independently of one another by a —CH═CH— or —C≡C— group;
- Cyc is cycloalkyl having 3-7 C atoms, in which 1-4 H atoms can be replaced independently from one another by A, Hal or OY;
- Hal is F, Cl, Br or I;
- and
- n is 0, 1, 2, 3, 4, 5 or 6;
- comprising the steps of:
- (a) heating to reflux temperature a phenol compound of formula (II)
- wherein R2, R3, R5 and R6 have the meaning as defined above,
- with 0.3 to 0.4 equivalents of hexamethylenetetramine in an organic acid,
- followed by adding a hydrolysis medium and heating the resulting mixture to yield a 4-hydroxy-benzaldehyde compound of formula (III)
- wherein R2, R3, R5 and R6 have the meaning as defined above,
- and
- (b) reacting the compound of formula (III) with an oxidizing agent in a solvent under acidic conditions to yield the compound of formula (I).
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Dependencies are inferred from the claim text.