Formic Acid → o-Xylene-3,alpha,alpha'-triol

HRID 597119Notes

Reaction equation

HRID 597119 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([OH:12])C(C)C.Cl.[CH:14](O)=[O:15]>[OH-].[Na+].C=O>[CH2:14]([C:3]1[C:2]([CH2:8][OH:12])=[C:1]([OH:7])[CH:6]=[CH:5][CH:4]=1)[OH:15]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 996PhenolHCID 6560Isobutanol

Product 1

HCID 81835o-Xylene-3,alpha,alpha'-triol

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

94 g of phenol are dissolved in 100 g of (33%) caustic soda solution and at 25° C 50 g of aqueous (30%) formaldehyde and 50 g of (90%) paraformaldehyde are added. The mixture initially heats slowly in an exothermic reaction. On reaching 40° C cooling takes place and this temperature is maintained until the formaldehyde content falls to below 1%, which takes 11/2 to 2 hours. 100 g of isobutanol are added and accompanied by cooling the mixture is set to a pH value of 8.0 to 8.5 with about 80 g of 35% hydrochloric acid, subsequently the pH value is set to 6.5 with about 5 to 10 g of formic acid, the aqueous phase is left to settle and discarded. The dimethylol phenol solution in isobutanol is freed from water by circulation distillation as described in Examples 1-4 under reduced pressure at 50°-55° C. Inorganic substances are removed by filtration and 240 g of the solution are obtained.

Workup

  1. additionare added
  2. customThe mixture initially heats slowly in an exothermic reaction
  3. customOn reaching 40° C
  4. temperaturecooling
  5. custom2 to 2 hours
  6. temperatureby cooling the mixture
  7. waitthe aqueous phase is left
  8. distillationThe dimethylol phenol solution in isobutanol is freed from water by circulation distillation
  9. customas described in Examples 1-4 under reduced pressure at 50°-55° C
  10. customInorganic substances are removed by filtration and 240 g of the solution
  11. customare obtained

Sources & evidence

ORD record
ord-f5300534a68a4b95bbd09ea054e1339c
Source dataset
uspto-grants-1977_03
Patent number
US04013605

Reaction notes

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