Hydrochloric Acid → 2-Methoxy-5,8-dihydronaphthalene-1,4-diol

HRID 726202ノート

反応式

HRID 726202 の反応式
[CH3:1][O:2][C:3]1[C:4](=[O:14])[CH:5]2[CH:10]([C:11](=[O:13])[CH:12]=1)[CH2:9][CH:8]=[CH:7][CH2:6]2.N#N.Cl>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([OH:13])[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[C:4]=1[OH:14]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 947Nitrogen2 回HCID 108215692-Methoxy-4a,5,8,8a-tetrahydronaphthalene-1,4-dione

生成物 1

HCID 53150632-Methoxy-5,8-dihydronaphthalene-1,4-diol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 2-methoxy-4a,5,8,8a-tetrahydronaphthalene-1,4-dione (55, 542 mg, 2.82 mmol) in MeOH (50 mL) was purged with a stream of N2 for 5 min with stirring at rt. With continued N2 purging, solid K2 CO3 (390 mg, 2.82 mmol, Baker) was added to the stirred solution. The solution immediately turned yellow. The reaction was allowed to stir for 15 min at rt under N2, after which it was brown. To this there was added a dilute HCl solution (10% concd HCl, 90% H2O, 50 mL) in one portion. The MeOH was removed in vacuo to give a colorless suspension. The suspended material was collected by filtration, washed with a dilute acid solution (as above, 4×6 mL) and dried in vacuo to yield a fluffy colorless solid (444 mg, 82%, pure by 1H NMR analysis (unstable on TLC)); mp 142.5°-144° C. (confirmed), lit. (Cavill et al., supra) 123°-124° C. (benzene/petroleum ether);

後処理

  1. stirringto stir for 15 min at rt under N2
  2. customThe MeOH was removed in vacuo
  3. customto give a colorless suspension
  4. filtrationThe suspended material was collected by filtration
  5. washwashed with a dilute acid solution (as above, 4×6 mL)
  6. customdried in vacuo
  7. customto yield a fluffy colorless solid (444 mg, 82%, pure by 1H NMR analysis (unstable on TLC))

出典と根拠

ORDレコード
ord-00b3ad87eb5e45008dbd06eb20aaeaa4
出典データセット
uspto-grants-1998_01
特許番号
US05708168

反応ノート

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