Hydrochloric Acid → HCID 20304527, compound

HRID 236956Notes

Reaction equation

HRID 236956 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:10][C:9]=1[OH:18])(=[O:7])[CH3:6].[Br:19]Br.Cl>ClCCl>[C:5]([C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)=[C:10]([Br:19])[C:9]=1[OH:18])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 109432711-(3-Hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Product 1

HCID 20304527HCID 20304527, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of aluminium chloride (8.15 g) and 7-acetyl-1,2,3,4-tetrahydro-6-hydroxynaphthalene (4.75 g) in dichloromethane (250 ml) was cooled to -10°. A solution of bromine (6.0 g) in dichloromethane (150 ml) was then added over 1 hour with constant stirring. The reaction mixture was allowed to warm to room temperature overnight, dilute HCl (400 ml) was added and the organic layer was separated, washed with water and dried (MgSO4). The solvent was filtered and the filtrate was evaporated to dryness leaving an oil which solidified on cooling to give 7-acetyl-5-bromo-1,2,3,4-tetrahydro-6-hydroxynaphthalene (5.3 g, 79%) mp 127°-130°.

Workup

  1. temperaturewas cooled to -10°
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationThe solvent was filtered
  6. customthe filtrate was evaporated to dryness
  7. customleaving an oil which
  8. temperatureon cooling

Sources & evidence

ORD record
ord-4766626657694bde9848851a09d67e61
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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