Water → HCID 15711987, compound

HRID 2292042Notes

Reaction equation

HRID 2292042 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][CH:9]2O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7]([CH3:14])([CH3:13])[CH:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 148194057-Bromo-1,2,3,4-tetrahydro-3,3-dimethyl-1-naphthalenol

Product 1

HCID 15711987HCID 15711987, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 7-bromo-3,3-dimethyl-1,2,3,4-tetrahydro-1-naphthol (7.0 g) and p-toluene sulphonic acid (0.5 g) in benzene (100 ml) was heated under reflux, using a Dean-Stark water separator, for 1.5 hours. After cooling, solvent was removed in vacuo, and the residue partitioned between ether and water. The combined ether extracts were washed with sodium bicarbonate solution, water, brine, then dried over sodium sulphate. Removal of drying agent and solvent gave the title compound as an oil (6.2 g) having:

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customsolvent was removed in vacuo
  4. customthe residue partitioned between ether and water
  5. washThe combined ether extracts were washed with sodium bicarbonate solution, water, brine
  6. dry with materialdried over sodium sulphate
  7. customRemoval
  8. customof drying agent and solvent

Sources & evidence

ORD record
ord-900ed1e873b942f68c1de2b475774613
Source dataset
uspto-grants-1989_01
Patent number
US04800212

Reaction notes

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