Benzeneacetic acid, 4-ethoxy- → HCID 28937799, compound

HRID 2375221Notes

Reaction equation

HRID 2375221 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)[CH3:2].C(O[C:17]1[CH:22]=[CH:21]C(CC(OC2CCCCO2)=O)=[CH:19][CH:18]=1)C>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]([OH:13])=[O:12])[CH2:21][CH2:22][CH2:17][CH2:18][CH2:19]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 78631Benzeneacetic acid, 4-ethoxy-HCID 69202066HCID 69202066, compound

Product 1

HCID 28937799HCID 28937799, compoundYield 40%

Procedure

The title compound was obtained in a manner analogous to that for 1-Phenylcyclohexanecarboxylic acid (1/3) starting with (4-ethoxyphenyl)acetic acid (4b), via tetrahydro-2H-pyran-2-yl 2-(4-ethoxyphenyl)acetate (5b). The crude product 1/5 was chromatographed on silica gel with toluene-ethyl acetate-acetic acid (9:1:0.1) as eluent to give 1-(4-ethoxyphenyl)cyclohexanecarboxylic acid (1/5) in 40% yield. 1H NMR (CDCl3, HMDSO) δ: 1H NMR (CDCl3, HMDSO) δ: 1.17-2.08 (8H, m); 1.34 (3H, t, J=7.0 Hz); 2.26-2.63 (2H, m); 4.02 (2H, q, J=7.0 Hz); 6.88 (2H, d, J=8.8 Hz); 7.36 (2H, d, J=8.8 Hz); 10.09 (1H, br s).

Workup

  1. customThe crude product 1/5 was chromatographed on silica gel with toluene-ethyl acetate-acetic acid (9:1:0.1) as eluent

Sources & evidence

ORD record
ord-bd8d4a6f567d4845b5359087ecf80215
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

Loading…