M-Cresol → Salicyl Alcohol

HRID 1703411Notes

Reaction equation

HRID 1703411 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1[C:13]([OH:14])=CC=CC=1C.C(C1C=C(O)C=CC=1)C.C=O>C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C([O-])=O.[Cd+2].C([O-])=O>[CH:4]1[CH:3]=[CH:2][C:1]([OH:7])=[C:6]([CH2:13][OH:14])[CH:5]=1

Participants

7

Reactant 4

HCID 342M-CresolHCID 712FormaldehydeHCID 996Phenol2×HCID 121013-Ethylphenol

Product 1

HCID 5146Salicyl Alcohol

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 197815Cadmium formateCatalyst

Procedure

Marchand and Grenet U.S. Pat. Nos. 3,290,352 and 3,290,393, patented Dec. 6, 1966, note that British Pat. No. 774,696 condenses phenol, meta-cresol or meta-ethylphenol with formaldehyde in aqueous medium in the presence of zinc acetate or cadmium formate. Starting with phenol, the best yield of pure saligenol obtained is 21%.

Sources & evidence

ORD record
ord-0fda863c31754c88be9ce0e0fa6edb63
Source dataset
uspto-grants-1982_09
Patent number
US04351962

Reaction notes

Loading…