Phenylacetone → 8-Acetyl-8-(2-methylphenyl)-12-hydroxyheptadecanoic Acid

HRID 1439482Notes

Reaction equation

HRID 1439482 reaction equation
CC1C=CC=CC=1CC(=O)C.C1(CC(=O)C)C=CC=CC=1.CC1C=CC=CC=1C(CCCC(OCC1C=CC=CC=1)CCCCC)C(=O)C.[C:50]([C:53]([C:82]1[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=1[CH3:88])([CH2:65][CH2:66][CH2:67][CH:68]([O:74]CC1C=CC=CC=1)[CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([O:62]CC)=[O:61])(=[O:52])[CH3:51].C(C(C1C=CC=CC=1C)(CCCC(OCC1C=CC=CC=1)CCCCC)CCCCCCC(O)=O)(=O)C.C(C(CCCC(O)CCCCC)CCCCCC(C1C=CC=CC=1C)C(O)=O)(=O)C>>[C:50]([C:53]([C:82]1[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=1[CH3:88])([CH2:65][CH2:66][CH2:67][CH:68]([OH:74])[CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([OH:62])=[O:61])(=[O:52])[CH3:51]

Participants

7

Reactant 6

HCID 7678PhenylacetoneHCID 27341091-(2-Methylphenyl)propan-2-oneHCID 21397387Ethyl 8-acetyl-8-(2-methylphenyl)-12-benzyloxyheptadecanoateHCID 213973918-Acetyl-8-(2-methylphenyl)-12-benzyloxyheptadecanoic acidHCID 213974048-Acetyl-(2-methylphenyl)-12-hydroxyheptadecanoic acidHCID 213974133-(2-Methylphenyl)-7-benzyloxy-2-dodecanone

Product 1

HCID 213974038-Acetyl-8-(2-methylphenyl)-12-hydroxyheptadecanoic Acid

Procedure

By following the procedures described in Example 3, but substituting (2-methyphenyl)acetone for the phenylacetone employed in Step C, there are obtained successively from that point: 3-(2-methylphenyl)-7-benzyloxy-2-dodecanone (Step C); ethyl 8-acetyl-8-(2-methylphenyl)-12-benzyloxyheptadecanoate (Step D); 8-acetyl-8-(2-methylphenyl)-12-benzyloxyheptadecanoic acid (Step E); and 8-acetyl-(2-methylphenyl)-12-hydroxyheptadecanoic acid (Step F).

Workup

  1. customare obtained successively from that point

Sources & evidence

ORD record
ord-7b33bd9c257540ff978d67faf35ef3d5
Source dataset
uspto-grants-1977_11
Patent number
US04059601

Reaction notes

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