Potassium Hydroxide → HCID 17867028, compound

HRID 1757474Notes

Reaction equation

HRID 1757474 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:18]=[C:19]([O:29][CH3:30])[C:20]=3[O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]([O:16]C)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[K+]>CO>[C:1]12([C:11]3[CH:12]=[C:13]([CH:18]=[C:19]([O:29][CH3:30])[C:20]=3[O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]([OH:16])=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19387995HCID 19387995, compound

Product 1

HCID 17867028HCID 17867028, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

18.32 g (58 mM) of the phenol obtained in Example 11(a) are treated with benzyl bromide under the conditions described in Example 5(a). After the same treatment, followed by chromatography on silica in the hexane/ether (90/10) eluent, there are isolated 15.26 g (59.6%) of methyl 3-(1-adamantyl)-4-benzyloxy-5-methoxybenzoate. 15.22 g (37.5 mM) of this ester in 150 ml of methanol are treated with 6.3 g of potassium hydroxide and are heated at reflux overnight. After the same treatment as in Example1(d), there are isolated 13.7 g (93.2%) of the expected derivative, of melting point 229° C.

Workup

  1. temperatureare heated
  2. temperatureat reflux overnight
  3. customAfter the same treatment as in Example1(d), there are isolated 13.7 g (93.2%) of the expected derivative, of melting point 229° C.

Sources & evidence

ORD record
ord-ef42781d878746c397c0c5524d27281a
Source dataset
uspto-grants-1995_08
Patent number
US05446059

Reaction notes

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