Dichloromethane → 3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 861795Notes

Reaction equation

HRID 861795 reaction equation
Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].ClCCl.[Al+3].[Cl-].[Cl-].[Cl-]>O>[Br:11][C:12]1[C:13]([OH:18])=[CH:14][C:15]2[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:2]([CH3:10])([CH3:3])[C:16]=2[CH:17]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 72442-BromophenolHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 107793113-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

36.6 g (0.2 mol) of 2,5-dichloro-2,5-dimethylhexane, 34.6 g (0.2 mol) of 2-bromophenol and 400 ml of dichloromethane were introduced successively into a three-necked flask. 26.6 g (0.2 mol) of AlCl3 were added in small amounts at 0° C. and stirring was carried out until gas evolution had ceased (violent reaction). The reaction mixture was poured into water and the organic phase was separated by settling, washed with an aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica column eluted with a mixture of ethyl acetate and heptane (10/90). After evaporating the solvents, 20.6 g (36%) of the expected phenol were recovered.

Workup

  1. custom(violent reaction)
  2. customthe organic phase was separated
  3. washwashed with an aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on a silica column
  7. washeluted with a mixture of ethyl acetate and heptane (10/90)
  8. customAfter evaporating the solvents, 20.6 g (36%) of the expected phenol
  9. customwere recovered

Sources & evidence

ORD record
ord-bcf77d8ef8a1431a8181af36e3c0aeab
Source dataset
uspto-grants-1998_02
Patent number
US05716624

Reaction notes

Loading…