Hydrochloric Acid → 1-Methyl-2,3-dihydroxy-naphthalene

HRID 745565Notes

Reaction equation

HRID 745565 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:13]=NNC(N)=O.[OH-].[K+].Cl>C(O)COCCO.O>[CH3:13][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:11]([OH:12])[C:2]=1[OH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1359884562,3-Dihydroxy-naphthaldehyde semicarbazone

Product 1

HCID 133438121-Methyl-2,3-dihydroxy-naphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

131 g of 2,3-dihydroxy-naphthaldehyde semicarbazone were boiled at reflux overnight with 250 g of powdered potassium hydroxide in 1350 ml of diethyleneglycol under an argon stream in a 1.5 l sulfonation flask equipped with stirrer, condenser, theremometer and calcium chloride tube. The cooled solution was diluted with 4,5 l of water, made acid with 450 ml of concentrated hydrochloric acid and extracted eight times with 1 l ether. The combined ether extracts were dried over sodium sulfate and evaporated in vacuo. Recrystallization from water gave 61.5 (65.5% of theory) of 1-methyl-2,3-dihydroxy-naphthalene. Melting point 97°-100° C.

Workup

  1. customequipped with stirrer, condenser
  2. extractionextracted eight times with 1 l ether
  3. dry with materialThe combined ether extracts were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customRecrystallization from water

Sources & evidence

ORD record
ord-5ed00a73e4f64e54bb24bb9a593dea6c
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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