4-(3-(2-Benzyloxyphenyl)propyl]benzoic acid → 4-[2-(2-Benzyloxyphenyl)-(Z)-ethenyl]-2-methoxybenzoic acid

HRID 2395018

Reaction equation

HRID 2395018 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[CH:16]\[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=CC=CC=1/C=C/C1C=CC(C(O)=O)=C(OC)C=1)C1C=CC=CC=1.C(OC1C=CC=CC=1CCCC1C=CC(C(OC)=O)=CC=1)C1C=CC=CC=1.C(OC1C=CC=CC=1CCCC1C=CC(C(O)=O)=CC=1)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[CH:16]\[C:17]1[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 189737644-(3-(2-Benzyloxyphenyl)propyl]benzoic acidHCID 189739004-[2-(2-benzyloxyphenyl)-(E)-ethenyl]-2-methoxybenzoic acidHCID 18973910Methyl 4-[3-(2-benzyloxyphenyl)propyl)benzoateHCID 70347226Methyl 4-[2-(2-benzyloxyphenyl)-(Z)-ethenyl]-2-methoxy-benzoate

Product 1

HCID 703468384-[2-(2-Benzyloxyphenyl)-(Z)-ethenyl]-2-methoxybenzoic acid

Procedure

Methyl 4-[2-(2-benzyloxyphenyl)-(Z)-ethenyl]-2-methoxy-benzoate (obtained from methyl 4-[2-(2-benzyloxyphenyl)-(Z)-ethenyl]-2-hydroxybenzoate as described in Example 14) was converted to 4-[2-(2-benzyloxyphenyl)-(E)-ethenyl]-2-methoxybenzoic acid (containing 15% of the (Z) isomer and obtained as a gum; negative FAB mass peak 359) using the method described in Example 1 for the conversion of methyl 4-[3-(2-benzyloxyphenyl)propyl]benzoate to 4-[3-(2-benzyloxyphenyl)-propyl]benzoic acid.

Workup

  1. customobtained as a gum

Sources & evidence

ORD record
ord-aecf430af043401fb443a1deb830d77a
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Linked notes

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