4-[3-(2-Hydroxy-4-cyanophenyl)propyl)benzoic acid → 4-[3-(2-Benzyloxy-4-cyanophenyl)propyl]benzoic acid

HRID 2395029Notes

Reaction equation

HRID 2395029 reaction equation
C(OC1C=C(C#N)C=CC=1C=O)C1C=CC=CC=1.[Br-].C(C1C=CC(CC[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1)(O)=O.[CH2:50]([O:57][C:58]1[CH:63]=[C:62]([C:64]#[N:65])[CH:61]=[CH:60][C:59]=1[CH:66]=[CH:67][CH2:68][C:69]1[CH:77]=[CH:76][C:72]([C:73]([OH:75])=[O:74])=[CH:71][CH:70]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(OC1C=C(C#N)C=CC=1CC=CC1C=CC(C(O)=O)=CC=1)C1C=CC=CC=1.OC1C=C(C#N)C=CC=1CCCC1C=CC(C(O)=O)=CC=1>>[CH2:50]([O:57][C:58]1[CH:63]=[C:62]([C:64]#[N:65])[CH:61]=[CH:60][C:59]=1[CH2:66][CH2:67][CH2:68][C:69]1[CH:70]=[CH:71][C:72]([C:73]([OH:75])=[O:74])=[CH:76][CH:77]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

6

Reactant 5

HCID 189737994-[3-(2-Hydroxy-4-cyanophenyl)propyl)benzoic acidHCID 189739062-Benzyloxy-4-cyanobenzaldehydeHCID 226755274-Carboxyphenethyltriphenylphosphonium bromideHCID 542188634-[3-(2-Benzyloxy-4-cyanophenyl)prop-1-enyl]benzoic acidHCID 703466874-[3-(2-Benzyloxy-4-cyanophenyl)prop-2-enyl]benzoic acid

Product 1

HCID 189741064-[3-(2-Benzyloxy-4-cyanophenyl)propyl]benzoic acid

Procedure

2-Benzyloxy-4-cyanobenzaldehyde and 4-carboxyphenethyltriphenylphosphonium bromide were converted to a mixture of 4-[3-(2-benzyloxy-4-cyanophenyl)prop-2-enyl]benzoic acid and 4-[3-(2-benzyloxy -4-cyanophenyl)prop-1-enyl]benzoic acid by a similar method to that of Example 1, (G). The alkenes were converted to the required 4-[3-(2-hydroxy-4-cyanophenyl)propyl)benzoic acid by a similar method to that of Example 33, Footnote a.

Sources & evidence

ORD record
ord-b296f06ab11d48a88af06741038b2158
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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