Catechol → 2-Ethyl-2-methyl-2H-1,3-benzodioxole

HRID 1033169Notes

Reaction equation

HRID 1033169 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][C:10](=O)[CH2:11][CH3:12].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)Cl>[CH2:10]([C:11]1([CH3:12])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)[CH3:9]

Participants

5

Reactant 3

HCID 289CatecholHCID 6569Methyl Ethyl KetoneHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 126081602-Ethyl-2-methyl-2H-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following Intermediate Method 3, the reaction of catechol with 2-butanone and phosphorus pentoxide in methylene chloride produces 2-ethyl-2-methyl-1,3-benzodioxole, (XVI). Nitration of (XVI) with nitric and sulfuric acid in methylene chloride yields 2-ethyl-2-methyl-5-nitro-1,3-benzodioxole, (XVII). Subsequent hydrogenation of the compound (XVII) with platinum oxide in ethanol produces 5-amino-2-ethyl-2-methyl-1,3-benzodioxole, (XVIII). ##STR30##

Sources & evidence

ORD record
ord-d4a2c283957342f69698cc36c704c909
Source dataset
uspto-grants-1994_05
Patent number
US05310724

Reaction notes

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