Resorcinol → 4,6-Bis(adamantyl)resorcinol

HRID 23003

반응식

HRID 23003 반응식
[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

참가 물질

4

반응물 2

HCID 5054Resorcinol2회HCID 791061-Bromoadamantane

생성물 1

HCID 235558344,6-Bis(adamantyl)resorcinol수율 66.8%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ca4c98bc324423185e05a742f255b62
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849696B2

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