تفاعل #82995

ord-6e93286652fb432280b5722491b4ec1d

معادلة التفاعل

CCCCBr
butyl bromide
O=c1c2ccc(O)cc2oc2cc(O)ccc12
3,6-Dihydroxy xanthone
O
water
O=c1c2ccc(O)cc2oc2cc(O)ccc12
3,6-dihydroxy xanthone
CCCCOc1ccc2c(=O)c3ccc(O)cc3oc2c1
3-Butoxy-6-hydroxyxanthone

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىwas controlled to 70° C
  2. 2
    workup.ADDITIONwas added dropwise
  3. 3
    ترشيحwas then filtered
  4. 4
    غسيلwashed with water
  5. 5
    workup.DISSOLUTIONThis precipitate was dissolved in 3% NaOH
  6. 6
    ترشيحfiltered
  7. 7
    أخرىfinally reprecipitated with HCl yielding 90% of 3-butoxy-6-hydroxy xanthone

الإجراء التجريبي

3,6-Dihydroxy xanthone (1,60.7 mmol) was dissolved into hot basic water (Na2CO3 240 mmol in 600 ml water). After the 3,6-dihydroxy xanthone was completely dissolved, the temperature was controlled to 70° C. Isopropyl alcohol (10 ml) was added to the reaction mixture and butyl bromide (180 mmol) was added dropwise. The reaction mixture was stirred rigorously for 72 hours. A white precipitate appeared which was then filtered and washed with water. There was almost no disubstituted compound in the product. This precipitate was dissolved in 3% NaOH, filtered and finally reprecipitated with HCl yielding 90% of 3-butoxy-6-hydroxy xanthone.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05623080uspto-grants-1997_04