1,4-Diacetylbenzene → HCID 22763540, compound

HRID 2071587Notes

Reaction equation

HRID 2071587 reaction equation
C(C1C=CC(C(=O)C)=CC=1)(=O)C.O.NN.[C:16]([C:19]1[CH:37]=[CH:36][C:22]([O:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](O)=[O:34])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)(O)=[O:17].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:34][CH2:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][CH2:25][CH2:24][O:23][C:22]2[CH:36]=[CH:37][C:19]([CH2:16][OH:17])=[CH:20][CH:21]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 138881,4-DiacetylbenzeneHCID 24654Hydrazine hydrate (1:1)HCID 77358Benzoic acid, 4,4'-[1,2-ethanediylbis(oxy)]bis-HCID 21226445Aluminium lithium hydride

Product 1

HCID 22763540HCID 22763540, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A bishydrazone was used in Ex. 26. It may be prepared by refluxing (48 hr) 1,4-diacetylbenzene with excess hydrazine hydrate in 2B alcohol, then cooling the reaction mixture to yield the product, m.p. = 184° C (dec.). The dialdehyde used in Ex. 35 is prepared by first reducing the dimethyl ester of 1,2-bis(4-carboxyphenoxy)ethane with lithium aluminum hydride in tetrahydrofuran to form 1,2-bis(4-hydroxymethylphenoxy)ethane; m.p. = 174°-176° C. The latter is oxidized to the desired dialdehyde with ceric ammonium nitrate in glacial acetic acid/water following the general procedure described in J. Org. Chem. 32, 3865-8 (1967); m.p. = 112.5°-114° C.

Workup

  1. customIt may be prepared
  2. temperaturecooling the reaction mixture
  3. customto yield the product, m.p. = 184° C (dec.)
  4. custom35 is prepared

Sources & evidence

ORD record
ord-367a22df8d7c450fb39863234baeef50
Source dataset
uspto-grants-1977_09
Patent number
US04048148

Reaction notes

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