1-Phenylcyclohexane-1-carboxylic acid → 2-(4-(Methoxycarbonyl)phenyl)acetic acid

HRID 2375225Notes

Reaction equation

HRID 2375225 reaction equation
C1(C[C:8]([O:10][CH:11]2CCCCO2)=[O:9])C=CC=CC=1.[C:17]1([C:23]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:11][O:10][C:8]([C:20]1[CH:21]=[CH:22][C:17]([C:23]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:18][CH:19]=1)=[O:9].[CH3:11][O:10][C:8]([C:20]1[CH:19]=[CH:18][C:17]([CH2:23][C:29]([OH:31])=[O:30])=[CH:22][CH:21]=1)=[O:9]

Participants

4

Reactant 2

HCID 708171-Phenylcyclohexane-1-carboxylic acidHCID 58611841HCID 58611841, compound

Product 2

HCID 107978792-(4-(Methoxycarbonyl)phenyl)acetic acidHCID 58611869HCID 58611869, compound

Procedure

The title compound was obtained from 2-[4-(methoxycarbonyl)phenyl]acetic acid (8a) by the method described above for tetrahydro-2H-pyran-2-yl 2-phenylacetate (5a) and 1-phenylcyclohexanecarboxylic acid (1/3). The crude product 1/4 was chromatographed on silica gel with toluene-ethyl acetate-acetic acid (8:2:0.1) as eluent to give 1-[4-(methoxycarbonyl)phenyl]-cyclohexanecarboxylic acid (1/4) in 68% yield (on 8a) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 0.94-2.09 (8H, m); 2.25-2.65 (2H, m); 3.88 (3H, s); 7.49 (2H, d, J=8.6 Hz); 7.96 (2H, d, J=8.6 Hz); 10.07 (1H, br s).

Workup

  1. customThe crude product 1/4 was chromatographed on silica gel with toluene-ethyl acetate-acetic acid (8:2:0.1) as eluent

Sources & evidence

ORD record
ord-a106ac0655ee423b98c150a8f61ae680
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

Loading…