Formaldehyde → HCID 12395600, compound

HRID 1287447Notes

Reaction equation

HRID 1287447 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 two hours, treated with DMF (30 ml.) and heated an additional 2 1/2 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 two hours
  2. temperatureheated an additional 2 1/2 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-65e296b4ffbb4a0cbae4068df9915aad
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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