Catechol → 1,3-benzodioxole-2-thione

HRID 2083679Notes

Reaction equation

HRID 2083679 reaction equation
[OH-].[Na+].[C:3]1([C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6])[OH:4].[C:11](Cl)(Cl)=[S:12]>>[O:4]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[O:6][C:11]1=[S:12]

Participants

4

Reactant 3

HCID 289CatecholHCID 10040ThiophosgeneHCID 14798Sodium Hydroxide

Product 1

HCID 6416061,3-benzodioxole-2-thione

Procedure

To 200 ml of aqueous sodium hydroxide (16.00 g, 0.400 mol) at 5° was added catechol (22.00 g, 0.200 mole). The resulting dark green solution was stirred magnetically and maintained at 5°-10° while thiophosgene (17 ml, 25.5 g, 0.22 mol) was added dropwise over 2 hours. The green color of the solution was discharged during the addition and an orange-brown precipitate formed. The mixture was filtered through a Buchner funnel into a saturated solution of aqueous sodium hydroxide to destroy any residual thiophosgene. The solid thus collected on the funnel was washed with 1.5 l of water and dried to give 27.41 (90 percent) of the crude 1,3-benzodioxole-2-thione (I): mp 151°-153° (sealed capillary; lit. mp 154°, 158°-158.5°). Sublimation twice at 150° (1 atm) gave white needles in 81 percent overall yield (lit. 25 percent): mp 158°-159.5° sealed capillary).

Workup

  1. additionwas added dropwise over 2 hours
  2. additionThe green color of the solution was discharged during the addition
  3. customan orange-brown precipitate formed
  4. filtrationThe mixture was filtered through a Buchner funnel into a saturated solution of aqueous sodium hydroxide
  5. customto destroy any residual thiophosgene
  6. customThe solid thus collected on the funnel
  7. washwas washed with 1.5 l of water
  8. customdried

Sources & evidence

ORD record
ord-d24987e8b6c043828f52de2be023b13c
Source dataset
uspto-grants-1978_04
Patent number
US04086265

Reaction notes

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