Phenol → 4,4-Bis(4-hydroxyphenyl)valeric acid

HRID 436191Notes

Reaction equation

HRID 436191 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([OH:15])(=[O:14])[CH2:9][CH2:10][C:11]([CH3:13])=O.[CH2:16](S)[CH3:17]>Cl.CCOCC>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([C:11]([C:17]2[CH:16]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)([CH3:13])[CH2:10][CH2:9][C:8]([OH:15])=[O:14])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 6343EthanethiolHCID 11579Levulinic Acid

Product 1

HCID 671744,4-Bis(4-hydroxyphenyl)valeric acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

376 g of phenol (4 mols), 116 g of levulinic acid (1 mol) and 0.4 ml of ethyl mercaptan were condensed, while stirring and simultaneously feeding in hydrogen chloride, for about 48 hours at 30°-40° C. The viscous reaction solution was taken up in ether and the ether phase was washed first with a sodium bicarbonate solution and then with water. After the ether had been eliminated, a brittle resin-like solid was obtained, m.p. 171°-173° C.

Workup

  1. customcondensed
  2. washthe ether phase was washed first with a sodium bicarbonate solution
  3. customa brittle resin-like solid was obtained

Sources & evidence

ORD record
ord-bcd3be6341a34d14a21855b92574cfde
Source dataset
uspto-grants-1977_02
Patent number
US04007282

Reaction notes

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