Dimethyl Sulfate → 3-Methoxybiphenyl

HRID 597266Notes

Reaction equation

HRID 597266 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.S(OC)(O[CH3:18])(=O)=O>[OH-].[K+].O>[CH3:18][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6497Dimethyl Sulfate2×HCID 113813-Phenylphenol

Product 1

HCID 2579713-Methoxybiphenyl

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14797Potassium HydroxideSolvent2×

Procedure

102 g of 3-hydroxy biphenyl are dissolved in a solution of 67.8 g of potassium hydroxide in 650 cc of water. 86.6 cc of dimethyl sulphate are added dropwise within 30 minutes while stirring, whereby the reaction mixture warms itself. The reaction mixture is then kept at 75° for a further 15 minutes. After 1 hour a further 33.6 g of potassium hydroxide in 45 cc of water are added dropwise, and subsequently 37.8 g of dimethyl sulphate are added dropwise at 65° within 15 minutes. The mixture is again kept at 75° for 1 hour. After cooling, the oily layer is separated and taken up in methylene chloride. Washing is effected once with 2 N sodium hydroxide and once with water. Extraction is again effected twice with methylene chloride. The organic phases are combined, dried over anhydrous sodium sulphate and concentrated. 3-methoxy biphenyl is obtained and is used for the next reaction step without purification.

Workup

  1. waitThe mixture is again kept at 75° for 1 hour
  2. temperatureAfter cooling
  3. customthe oily layer is separated
  4. washWashing
  5. extractionExtraction
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b9fd85e041734a2da3b58e6f00dda087
Source dataset
uspto-grants-1977_03
Patent number
US04013690

Reaction notes

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