1,8-Octanediamine → Naphthalene

HRID 987609Notes

Reaction equation

HRID 987609 reaction equation
O[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5](O)[CH:6]=[C:7](S(O)(=O)=O)[CH:8]=2)[CH:3]=1.S([O-])(O)=O.[Na+].NCCCCCCCCN>O>[CH:8]1[C:9]2[C:4](=[CH:3][CH:2]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 242501,8-OctanediamineHCID 806744,6-Dihydroxynaphthalene-2-sulfonic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 931Naphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Step 4) 2,8-Dihydroxy naphthalene-6-sulfonic acid (263 parts), sodium hydrogen sulphite (259 parts), water (900 parts) and 1,8-diaminooctane (400 parts) were stirred at 80° C. for 20 hours and then a further 20 hours at 95° C. The reaction was allowed to cool over night and filtered. The resultant filter cake was stirred in water (500 parts) and 2N sodium hydroxide (750 parts) for 15 minutes. 2N Hydrochloric acid (300 parts) was added and the precipitate filtered. The filter cake was dissolved in water (500 parts) and 2N sodium hydroxide (1000 parts) by heating to 50° C. 2N Hydrochloric acid was added and the precipitate filtered off at 40° C. The filter cake was oven dried at 70° C. to produce a naphthalene intermediate (111 parts).

Workup

  1. customa further 20 hours
  2. customat 95° C
  3. temperatureto cool over night
  4. filtrationfiltered
  5. filtrationThe resultant filter cake
  6. addition2N Hydrochloric acid (300 parts) was added
  7. filtrationthe precipitate filtered
  8. dissolutionThe filter cake was dissolved in water (500 parts)
  9. addition2N Hydrochloric acid was added
  10. filtrationthe precipitate filtered off at 40° C
  11. customdried at 70° C.

Sources & evidence

ORD record
ord-09b76c42cbe5447ab4a895b9697e1988
Source dataset
uspto-grants-2003_10
Patent number
US06632858B1

Reaction notes

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