Benzyl Chloride → Dibenzyl 2,3-bis(benzyloxy)terephthalate

HRID 59181

反応式

HRID 59181 の反応式
[OH:1][C:2]1[C:10]([OH:11])=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:15]([O:1][C:2]1[C:10]([O:11][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]([C:12]([O:14][CH2:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=2)=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 882732,3-Dihydroxyterephthalic acid

生成物 1

HCID 118136033Dibenzyl 2,3-bis(benzyloxy)terephthalate収率 48%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
67 °C

実験手順

1 (101.798 g, 0.514 mol), benzyl chloride (258 mL, 2.242 mol), KI (25.304 g, 0.140 mol), K2CO3 (664.270 g, 4.806 mol), and 1.3 L DMF were combined in a 5-L 3-neck round-bottom flask, yielding a mixture of dark brown solution and undissolved solid. The flask was fitted with a reflux condenser and mechanical stirrer, and placed in a heating mantle. The reaction mixture was heated at 67° C. for 3 d and filtered. The dark brown, clear filtrate was rotovapped to ˜400 mL of opaque, brown, viscous oil, which was dissolved in ˜600 mL DCM. The opaque, brown solution was filtered and extracted with water (5×500 mL). A small amount of brine was used to break up emulsions. The organic layer was dried with MgSO4 and rotovapped to ˜250 mL of dark brown oil. This oil was purified by silica column chromatography (0-5% MeOH in DCM) to yield a hardened brown oil (48%).

後処理

  1. customyielding
  2. additiona mixture of dark brown solution
  3. customThe flask was fitted with a reflux condenser and mechanical stirrer
  4. filtrationfiltered
  5. dissolutionbrown, viscous oil, which was dissolved in ˜600 mL DCM
  6. filtrationThe opaque, brown solution was filtered
  7. extractionextracted with water (5×500 mL)
  8. dry with materialThe organic layer was dried with MgSO4
  9. customThis oil was purified by silica column chromatography (0-5% MeOH in DCM)

出典と根拠

ORDレコード
ord-eeb610df79ef4d38baac448a9bd8ddae
出典データセット
uspto-grants-2016_09
特許番号
US09439984B2

関連ノート

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