Hexanoyl chloride → HCID 4347284, compound

HRID 616985Notes

Reaction equation

HRID 616985 reaction equation
O([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:15](Cl)(=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[OH2:23].C(Cl)Cl>[OH-].[Na+]>[O:21]([C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:13](=[O:23])[CH2:14][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][CH:13]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 67340Hexanoyl chlorideHCID 18616509HCID 18616509, compoundHCID 21908982Water methylene chloride

Product 1

HCID 4347284HCID 4347284, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of p-phenoxyaminobenzene (3.4g, 0.019 mole) in aqueous sodium hydroxide (100 ml. 12% NaOH) was stirred magnetically. Hexanoyl chloride (2.80g, 0.021 mole) was added dropwise over five minutes. The suspension was stirred for one hour and shaken with water-methylene chloride. The organic layer was washed twice with water, dried over anh. sodium sulphate and evaporated to dryness, in vacuo. Weight of beige solid; 4.30g, 81%, m.p. 69°-76° C. A portion (4.14g) was crystallized from chloroform-hexane, filtered and dried for 16 hours at 48° C./10 mm. Weight of beige solid -- 2.24g, m.p. 96°-98.5° C., sinters at 93° C. Recrystallized from the same solvents gave 1.90g beige crystals, m.p. 98.5°-99.5° C.

Workup

  1. stirringThe suspension was stirred for one hour
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over anh. sodium sulphate
  4. customevaporated to dryness, in vacuo
  5. customA portion (4.14g) was crystallized from chloroform-hexane
  6. filtrationfiltered
  7. customdried for 16 hours at 48° C./10 mm
  8. customat 93° C
  9. customRecrystallized from the same solvents

Sources & evidence

ORD record
ord-113aa9c9cf9d4f16a80668cee728e6a1
Source dataset
uspto-grants-1978_02
Patent number
US04076849

Reaction notes

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