Methanol → HCID 87133463, compound

HRID 337396Notes

Reaction equation

HRID 337396 reaction equation
[CH:1]1[C:10]2[O:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:15][CH2:16][C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:24][OH:25].Cl[CH2:27][Cl:28]>>[CH:11]1[C:8]2[O:9][C:10]3[CH:1]=[CH:2][C:3]([C:24](=[O:25])[CH2:27][Cl:28])=[CH:4][C:5]=3[O:6][C:7]=2[CH:14]=[CH:13][C:12]=1[C:17](=[O:18])[CH2:16][Cl:15]

Participants

6

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 9216Dibenzo-p-dioxinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 87133463HCID 87133463, compound

Conditions

Temperature
-78 °C

Procedure

Dibenzo[b,e][1,4]dioxine (2 g, 10.86 mmol), was taken in dichloromethane (10 ml), 2-chloroacetyl chloride (2.0 ml, 24.97 mmol) was added and the reaction was cooled to −78° C. Aluminium chloride (5.79 g, 43.4 mmol) was added carefully and was stirred for additional 2 h at −78° C., then slowly allowed to reach rt and stirred for additional 2 h. Cooled to 0° C. and ice was added, stirred for few min, white precipitation noticed, MeOH (5 mL) was added and stirred for 1 h. The precipitate was filtered and washed with water and used in the next step. Yield: 1.8, 50%; ES LC-MS m/z=337 (M−H+);

Workup

  1. customto reach rt
  2. stirringstirred for additional 2 h
  3. temperatureCooled to 0° C.
  4. additionice was added
  5. stirringstirred for few min, white precipitation
  6. stirringstirred for 1 h
  7. filtrationThe precipitate was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-d72030cbda484be3b20627f0064077b6
Source dataset
uspto-grants-2014_11
Patent number
US08889726B2

Reaction notes

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