Dimethyl Sulfoxide → 5,8-Dihydro-1-naphthyl benzyl ether

HRID 2082778Notes

Reaction equation

HRID 2082778 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CS(C)=O.C[O-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([O:11][C:1]1[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 974665,8-Dihydro-1-naphtholHCID 10942334Sodium Methoxide

Product 1

HCID 203605175,8-Dihydro-1-naphthyl benzyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 73 g. (0.5 m) of 5,8-dihydro-1-naphthol in 100 ml. DMSO is treated with 0.5 m sodium methoxide. The mixture is cooled in an ice bath and treated dropwise with 0.5 mole benzyl bromide with shaking periodically. The mixture is gradually allowed to warm up to about 45° toward the end of addition. The mixture is stirred 3 hrs. longer, then poured into 1 liter H2O and extracted into ether. Extracts are washed twice with 10% NaOH, dried, taken to dryness leaving almost a quantitative yield of crystalline 5,8-dihydro-1-naphthyl benzyl ether.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. temperatureto warm up to about 45° toward the end of addition
  3. stirringThe mixture is stirred 3 hrs
  4. extractionextracted into ether
  5. washExtracts are washed twice with 10% NaOH
  6. customdried

Sources & evidence

ORD record
ord-362c38255649468bbe994c113250316f
Source dataset
uspto-grants-1978_04
Patent number
US04082773

Reaction notes

Loading…