Hydroxide → 4-Hydroxy-4'-methoxybiphenyl

HRID 1761658Notes

Reaction equation

HRID 1761658 reaction equation
C([C:4]1[C:5]([OH:17])=[CH:6][C:7]2C[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH3:16])[C:12]=2[CH:13]=1)(=O)C.[OH-].S(OC)([O:22][CH3:23])(=O)=O>>[CH3:23][O:22][C:16]1[CH:9]=[CH:10][C:11]([C:12]2[CH:13]=[CH:4][C:5]([OH:17])=[CH:6][CH:7]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 961HydroxideHCID 6497Dimethyl SulfateHCID 212421503-Acetyl-5-propyl-5,6,7,8-tetrahydro-2-naphthol

Product 1

HCID 110308394-Hydroxy-4'-methoxybiphenyl

Procedure

4,4'-Dihydroxydiphenyl (1) (32 g 0.17 mol) was dissolved in 2M solution hydroxide solution (0.34 mol) and dimethyl sulphate (22 g 0.175 mol) was added slowly with stirring over half an hour. The sodium salt of the required product was filtered off and dried. The yield was 24 g. The sodium salt of the phenol (24 g) was treated with acetyl chloride (150 cm3), filtered and excess acetyl chloride removed. Work up gave 4- methoxy-4'-acetoxydiphenyl (4) (22 g).

Workup

  1. additionwas added slowly
  2. filtrationThe sodium salt of the required product was filtered off
  3. customdried
  4. additionThe sodium salt of the phenol (24 g) was treated with acetyl chloride (150 cm3)
  5. filtrationfiltered
  6. customexcess acetyl chloride removed

Sources & evidence

ORD record
ord-712fec2504a749cfa2b8a87ad88f1ffa
Source dataset
uspto-grants-1989_05
Patent number
US04826977

Reaction notes

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