Resorcinol → 4,6-Bis(adamantyl)resorcinol

HRID 23003

Reaction equation

HRID 23003 reaction equation
[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

Participants

4

Reactant 2

HCID 5054Resorcinol2×HCID 791061-Bromoadamantane

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9ca4c98bc324423185e05a742f255b62
Source dataset
uspto-grants-2005_02
Patent number
US06849696B2

Linked notes

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