Bromine → 1,1,3,4,4,6-Hexamethyl-7-bromacetyl-1,2,3,4-tetrahydronaphthalene

HRID 1730359

Reaction equation

HRID 1730359 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[C:9]([C:12](=[O:14])[CH3:13])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[CH:4]([CH3:18])[CH2:3]1.[Br:20]Br>C(O)(=O)C>[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[C:9]([C:12](=[O:14])[CH2:13][Br:20])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[CH:4]([CH3:18])[CH2:3]1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 89440Tonalide

Product 1

HCID 214306251,1,3,4,4,6-Hexamethyl-7-bromacetyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1,1,3,4,4,6-Hexamethyl-7-acetyl-1,2,3,4-tetrahydronaphthalene(33 g.) in 40 ml. glacial acetic acid was treated slowly with 20 g. bromine. Warming was necessary to initiate the reaction, evidenced by disappearance of the red colouration. When all the bromine had been added,the mixture was cooled and poured onto ice to give a pale green gum. The whole was extracted with ether, the ethereal extracts washed with dilute Na2CO3, water and finally dried over MgSO4. Evaporation ofthe ether gave a pale green solid which was recrystallised from EtOH to give the title compound 27.6 g. (64%), m.p. 68° C. Analysis : Calculated for C18H25OBr, C, 64.09%; H, 7.47%. Found : C, 64.40%; H, 7.65%.

Workup

  1. temperatureWarming
  2. customthe reaction
  3. temperaturewas cooled
  4. additionpoured onto ice
  5. customto give a pale green gum
  6. extractionThe whole was extracted with ether
  7. washthe ethereal extracts washed with dilute Na2CO3, water
  8. dry with materialfinally dried over MgSO4
  9. customEvaporation ofthe ether
  10. customgave a pale green solid which
  11. customwas recrystallised from EtOH

Sources & evidence

ORD record
ord-a0b777b7048d4fe2aa51455fe7b692c7
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Linked notes

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