2-Naphthoic acid → 1,2,3,4-Tetrahydro-2-naphthoic acid

HRID 1413

Reaction equation

HRID 1413 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].[Na].C(OCCOCC)C>>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 3

HCID 71232-Naphthoic acidHCID 12375Ethylene glycol diethyl etherHCID 5360545Sodium

Product 1

HCID 1013701,2,3,4-Tetrahydro-2-naphthoic acid

Procedure

The thus obtained 6-[4'-alkoxy-4-biphenyl)ethyl]-2-naphthalenecarboxylic acid (22) is hydrogenated in the presence of metal sodium in a solvent such as 1,2-diethoxyethane to obtain 6-[4'-alkoxy-4-biphenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (23). Finally, the resulting 6-[4'-alkoxy-4-biphenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (23) is reacted with an alcohol (24) having an asymmetric carbon in the presence of 4-N,N-dimethylaminoprydine, whereby the above-mentioned carboxylate compound (25) represented by the formula (II), in which x is --CH2CH2 --, may be obtained.

Sources & evidence

ORD record
ord-bf36940ac45c47b1a49e30e635325cb5
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Linked notes

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