Hydrochloric Acid → 5-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

HRID 259007Notes

Reaction equation

HRID 259007 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[ClH:13].[CH2:14]=O>>[Cl:13][CH2:14][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 123936195-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Procedure

To a mixture of 20 g. of 6-hydroxy-3,4-dihydro-1(2H)-naphthalenone and 110 ml. of concentrated hydrochloric acid is added 4.6 g. of paraformaldehyde and the mixture is agitated at room temperature for 20 hours. To the reaction mixture is added 200 ml. of water, and the resulting precipitate is recovered by filtration, rinsed with water and benzene and dried. The described procedure provides 5-chloromethyl-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone. Yield 21 g.; melting point: 172°-174° C (decomp.).

Workup

  1. additionTo a mixture of 20 g
  2. additionTo the reaction mixture is added 200 ml
  3. filtrationof water, and the resulting precipitate is recovered by filtration
  4. washrinsed with water and benzene
  5. customdried

Sources & evidence

ORD record
ord-afc85db18d2d4bd59d7ccbe880851a60
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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