Resorcinol → 4,6-Bis(adamantyl)resorcinol

HRID 23003

反応式

HRID 23003 の反応式
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Br[C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2>C1(C)C=CC=CC=1>[C:10]12([C:6]3[CH:7]=[C:8]([C:10]45[CH2:19][CH:14]6[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]6)[CH2:11]4)[CH2:17]5)[C:1]([OH:2])=[CH:3][C:4]=3[OH:5])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2

参加物

4

反応物 2

HCID 5054Resorcinol2 回HCID 791061-Bromoadamantane

生成物 1

HCID 235558344,6-Bis(adamantyl)resorcinol収率 66.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

Into a 250-mL 3-neck flask, equipped with nitrogen inlet, thermocouple and condenser, were added resorcinol (11.00 g, 100.0 mMol), bromoadmantane (44.02 g, 205.1 mMol) and toluene (150 mL). The mixture was heated to 110° C. and became a clear solution. The reaction was allowed to continue for 48 h, at which time TLC showed that all the resorcinol had disappeared. The solvent was removed and the solid was crystallized from hexanes (150 mL). The disubstituted product was obtained in 66.8% yield (25.26 g) as a white solid. Another 5.10 g product was obtained by silica gel column chromatography of the concentrated mother liquor after the first crop. The total yield of the product was 80.3%. Characterization of the product was by proton NMR, HPLC, FTIR and MS.

後処理

  1. customInto a 250-mL 3-neck flask, equipped with nitrogen inlet
  2. customThe solvent was removed
  3. customthe solid was crystallized from hexanes (150 mL)
  4. customThe disubstituted product was obtained in 66.8% yield (25.26 g) as a white solid

出典と根拠

ORDレコード
ord-9ca4c98bc324423185e05a742f255b62
出典データセット
uspto-grants-2005_02
特許番号
US06849696B2

関連ノート

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