Formaldehyde → HCID 12395600, compound

HRID 596997Notes

Reaction equation

HRID 596997 reaction equation
ClC1C(Cl)=C(C(=O)CCCCCBr)C=CC=1OC.Cl.CNC.C=O.[Cl:25][C:26]1[C:31]([Cl:32])=[C:30]([C:33](=[O:41])[C:34](=[CH2:40])[CH2:35][CH2:36][CH2:37][CH2:38][Cl:39])[CH:29]=[CH:28][C:27]=1[O:42][CH3:43].S(=O)(=O)(O)O>O.CN(C=O)C.C(O)(=O)C>[Cl:39][CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[CH2:40][C:29]2[C:30](=[C:31]([Cl:32])[C:26]([Cl:25])=[C:27]([O:42][CH3:43])[CH:28]=2)[C:33]1=[O:41]

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 1118Sulfuric Acid2×HCID 10473Dimethylamine, hydrochlorideHCID 12395598HCID 12395598, compoundHCID 12395599HCID 12395599, compound

Product 1

HCID 12395600HCID 12395600, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2,3-dichloro-4-(6-bromohexanoyl)anisole (10 g.), dimethylamine hydrochloride (4 g.), paraformaldehyde (2 g.) and acetic acid (0.5 ml.) is heated on a steam bath for 2 hours, treated with DMF (30 ml.)' and heated an additional 2.5 hours. The reaction mixture is poured into water, extracted with ether, washed with water and dried over magnesium sulfate. Evaporation of the ether affords 9 g. of crude 2,3-dichloro-4-(6-chloro-2-methylenehexanoyl)anisole which is cyclialkylated by treatment with concentrated sulfuric acid (50 ml.). The sulfuric acid solution is poured into water (300 ml.) affording 5.8 g. of 2-(4-chlorobutyl)-5-methoxy-6,7-dichloro-1-indanone which melts at 92° C. after recrystallization from cyclohexane.

Workup

  1. temperatureis heated on a steam bath for 2 hours
  2. temperatureheated an additional 2.5 hours
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the ether
  7. customaffords 9 g
  8. customaffording 5.8 g
  9. customof 2-(4-chlorobutyl)-5-methoxy-6,7-dichloro-1-indanone which melts at 92° C. after recrystallization from cyclohexane

Sources & evidence

ORD record
ord-2684fb83a45c4236ad0b8a868d9647c3
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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