Benzyl Bromide → 3-Benzyloxy-4-(1-adamantyl)benzoic acid

HRID 1757471Notes

Reaction equation

C(Br)C1C=CC=CC=1.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[C:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2)[C:20]([O:22]C)=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[C:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2)[C:20]([OH:22])=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 19387981Methyl 3-benzyloxy-4-(1-adamantyl)benzoate

Product 1

HCID 178670343-Benzyloxy-4-(1-adamantyl)benzoic acid

Procedure

18 g (63 mM) of the ester obtained in Example 9(a) are treated with benzyl bromide under the conditions described in Example 5(a) to lead, after the same treatment, to 17.5 g (74%) of methyl 3-benzyloxy-4-(1-adamantyl)benzoate. The derivative obtained is then saponified under the conditions described in Example 7(b) to lead, after the same treatment, to 13.6 g (96.6%) of the expected derivative, of melting point 240° C.

Workup

customThe derivative obtained

Sources & evidence

ORD record: ord-cdab5e5c805e496ca49a6b779eea4dea
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05446059

Reaction notes

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