Hexanoic Acid → HCID 14574144, compound

HRID 1638935Notes

Reaction equation

HRID 1638935 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([OH:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1CCC(N=C=NC2CCCCC2)CC1.[C:36](O)(=[O:42])[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C1C=CN=CC=1)C>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([CH:18]([O:20][C:36](=[O:42])[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH3:19])=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 14297725HCID 14297725, compound2×

Product 1

HCID 14574144HCID 14574144, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Racemic (±)-4-pentyl-4'-(1-hydroxyethyl)biphenyl (m.p. 90.0° C.) was optically resolved by biochemical transesterification. Using the obtained 5.0 g of (-)-4- pentyl-4'-(1-hydroxyethyl)biphenyl (m.p. 83.8° C., [α]D 24.5 -25.0° (c 1.0, CH3OH)), 7.0 g of DCC, 1.0 g of DMAP and 3.0 g of caproic acid, optically active 4-pentyl-4'-(1-hexanoyloxyethyl)biphenyl 3.2 g was obtained by the same method as described in Example 1. The melting point of the obtained biphenyl was 10° C.

Sources & evidence

ORD record
ord-3517aea40a3742378dbb2bfb20373335
Source dataset
uspto-grants-1989_11
Patent number
US04882084

Reaction notes

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