Hydrochloric Acid → Benzyl 6-[3-(1-adamantyl)-4-methoxycarbonylmethyloxyphenyl]-2-naphthoate

HRID 1078493Notes

Reaction equation

HRID 1078493 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[CH:24]=[CH:23]5)[CH:16]=[CH:17][C:18]=3[OH:19])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.Br[CH2:41][C:42]([O:44][CH3:45])=[O:43].Cl>CN(C=O)C>[C:3]12([C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[O:31])[CH:24]=[CH:23]5)[CH:16]=[CH:17][C:18]=3[O:19][CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:9]([CH2:11]3)[CH2:10]1)[CH2:12]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10672648Benzyl 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthoate

Product 1

HCID 19429712Benzyl 6-[3-(1-adamantyl)-4-methoxycarbonylmethyloxyphenyl]-2-naphthoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

136 mg of 80% sodium hydride in oil are added to a solution of 8 g (16mmol) of benzyl 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthoate in 100 ml of DMF. The mixture is left stirring for 1 h and 1.6 ml (16.4 mmol) of methyl bromoacetate are added. The reaction mixture is left stirring overnight, and it is then poured into ice cold water and acidified to pH 2 with concentrated HCl. The solid is filtered and recrystallized from ether. 8.52 g (95%) of the expected derivative are recovered, which derivative melts at 183° C.

Workup

  1. waitThe mixture is left
  2. waitThe reaction mixture is left
  3. stirringstirring overnight
  4. additionit is then poured into ice cold water
  5. filtrationThe solid is filtered
  6. customrecrystallized from ether
  7. custom8.52 g (95%) of the expected derivative are recovered

Sources & evidence

ORD record
ord-5d276a718e7441df98747ff9e46c5aaa
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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