Water → 1,2-Benzenedimethanol

HRID 1730716Notes

Reaction equation

HRID 1730716 reaction equation
[C:1]1(CCl)[C:2](CCl)=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:11]([O-:14])(=O)[CH3:12].[Na+].C(N(CC)CC)C.[Cl-].[Na+].[OH2:25]>ClC1C=CC=CC=1>[C:12]1([CH2:11][OH:14])[C:6]([CH2:5][OH:25])=[CH:1][CH:2]=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 962WaterHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 119191,2-Bis(chloromethyl)benzeneHCID 517045Sodium Acetate

Product 1

HCID 691531,2-BenzenedimethanolYield 94%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent3×

Conditions

Temperature
100 °C

Procedure

Into a four-neck flask provided with a reflux condenser, thermometer, dropping funnnel, and stirrer, were charged 40 parts of o-xylylene dichloride of 99.8% purity, 40 parts of anhydrous sodium acetate, and 20 parts of monochlorobenzene. Into the flask was added with stirring at 100° C., 0.8 part of triethylamine. Esterification was allowed to proceed at 97° to 101° C. for 10 hours. To the reaction mixture was added 100 parts of warm water to dissolve the by-product sodium chloride. The mixture was left standing to allow it to settle in monochlorobenzene layer and aqueous layer. To the monochlorobenzene layer which had been freed from the catalyst amine by removing with 2.6 parts of 30-% sulfuric acid, were added 19.4 parts of sodium hydroxide and 170 parts of water. Saponification was allowed to proceed at 94° C. for 2 hours. After saponification, the reaction mixture was neutralized with 3N hydrochloric acid and left standing at 85° C. to allow the mixture to settle in two layers. Without having been freed from impurities, the aqueous layer containing o-xylylene glycol was extracted three times with ethyl acetate in a manner similar to that in Example 1. The ethyl acetate extracts were combined, distilled to recover ethyl acetate, and dried in vacuo to obtain 29.6 parts of o-xylylene glycol (melting point, 60.7° - 62° C.) in a yield of 94.0%.

Workup

  1. customInto a four-neck flask provided with a reflux condenser
  2. additionInto the flask was added
  3. waitThe mixture was left
  4. customby removing with 2.6 parts of 30-% sulfuric acid
  5. additionwere added 19.4 parts of sodium hydroxide and 170 parts of water
  6. waitto proceed at 94° C. for 2 hours
  7. waitleft
  8. customstanding at 85° C.
  9. additionthe aqueous layer containing o-xylylene glycol
  10. extractionwas extracted three times with ethyl acetate in a manner similar to that in Example 1
  11. distillationdistilled
  12. customto recover ethyl acetate
  13. customdried in vacuo

Sources & evidence

ORD record
ord-5a9ce37dd09e4c94a3b2f7fbfbb90b5c
Source dataset
uspto-grants-1976_11
Patent number
US03993699

Reaction notes

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