4-(4-Octyloxyphenyl)benzoyl chloride → 4-(2-Pentanoyloxy-1-keto-propyl)-phenyl 4'-octyloxybiphenyl-4-ylcarboxylate

HRID 373463Notes

Reaction equation

HRID 373463 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22](Cl)=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(C1C=CC(C2C=CC(C(OC(C)C(C3C=CC(OCC=C)=CC=3)=O)=O)=CC=2)=CC=1)CCCCCC.[C:61]([O:67][CH:68]([CH3:78])[C:69]([C:71]1[CH:76]=[CH:75][C:74]([OH:77])=[CH:73][CH:72]=1)=[O:70])(=[O:66])[CH2:62][CH2:63][CH2:64][CH3:65]>CN(C1C=CN=CC=1)C>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:77][C:74]3[CH:75]=[CH:76][C:71]([C:69](=[O:70])[CH:68]([O:67][C:61](=[O:66])[CH2:62][CH2:63][CH2:64][CH3:65])[CH3:78])=[CH:72][CH:73]=3)=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 198100571-Methyl-2-(4'-allyloxy-phenyl)-2-keto-ethyl 4'-heptylbiphenyl-4-ylcarboxylateHCID 198101294-(2-Pentanoyloxy-1-keto-propyl)phenol

Product 1

HCID 198100404-(2-Pentanoyloxy-1-keto-propyl)-phenyl 4'-octyloxybiphenyl-4-ylcarboxylate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of 500 mg of 4'-octyloxy-biphenyl-4-yl-carboxylic acid chloride, 400 mg of (S) 4-(2-pentanoyloxy-1-keto-propyl)phenol, 600 mg of N,N-dicyclohexylcarbodiimide, and 20 mg of DMAP was stirred at room temperature for three hours. A solid material precipitated was removed by filtration. The organic layer thus obtained was washed with an acid, an alkali, and with water, dried, and then concentrated.

Workup

  1. customA solid material precipitated
  2. customwas removed by filtration
  3. customThe organic layer thus obtained
  4. washwas washed with an acid
  5. dry with materialan alkali, and with water, dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af6d64d2a7ba4b25a4acd3588fc4cde5
Source dataset
uspto-grants-1992_11
Patent number
US05164112

Reaction notes

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