HCID 15685334, compound → 4-(Hexadecylamino)benzoic acid

HRID 2049845Notes

Reaction equation

HRID 2049845 reaction equation
[CH2:1]([NH:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:18](NC1C=CC(CO)=CC=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]C.C(NC1C=CC(C[OH:52])=CC=1)CCCCCCCCC.C(NC1C=CC(CO)=CC=1)CCCCCCCCCC.C(NC1C=CC(CO)=CC=1)CCCCCCCCCCC.C(NC1C=CC(CO)=CC=1)CCCCCCCCCCCC.C(NC1C=CC(CO)=CC=1)CCCCCCCCCCCCCC.CC(C)CCCCCCCCCCCCCNC1C=CC(CO)=CC=1.C(NC1C=CC(CO)=CC=1)CCCCCCCCCCCCCCCC.C(NC1C=CC(CO)=CC=1)CCCCCCCCCCCCCCCCC.C(NC1C=CC(CO)=CC=1)CCCCCCCCCCCCCCCCCC>>[CH2:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:52])=[O:15])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

12

Reactant 11

HCID 15685334HCID 15685334, compoundHCID 53825474HCID 53825474, compoundHCID 53837907HCID 53837907, compoundHCID 53999468HCID 53999468, compoundHCID 54003627HCID 54003627, compoundHCID 54074147HCID 54074147, compoundHCID 54250571HCID 54250571, compoundHCID 54258385HCID 54258385, compoundHCID 54276733HCID 54276733, compoundHCID 54515173HCID 54515173, compoundHCID 54547974HCID 54547974, compound

Product 1

HCID 472634-(Hexadecylamino)benzoic acid

Procedure

p-Hexadecylaminobenzoic acid (2.0 g.) is dissolved in 20 ml. of dry tetrahydrofuran, and to this is added portionwise at room-temperature 0.5 g. of lithium aluminum hydride. The mixture is stirred at room temperature for 3 hours, and then is quenched with 10% aqueous ammonium chloride solution. The mixture is filtered, and the filtrate is evaporated in vacuo to provide a yellow solid. The residue is extracted several times with methylene chloride and the extracts are evaporated in vacuo to give a white solid. Recrystallization from hexane gave the product of the Example, m.p. 74°-75° C. Replacement of p-hexadecylaminobenzoic acid with p-octylaminobenzoic acid, p-nonylaminobenzoic acid, p-decylaminobenzoic acid, p-undecylaminobenzoic acid, p-dodecylaminobenzoic acid, p-tridecylaminobenzoic acid, p-(14-methylpentadecyl)aminobenzoic acid, p-pentadecylaminobenzoic acid, p-heptadecylaminobenzoic acid, p-octadecylaminobenzoic acid, and nondecylaminobenzoic acid provide respectively, p-octylaminobenzyl alcohol, p-nonylaminobenzyl alcohol, p-decylaminobenzyl alcohol, p-undecylaminobenzyl alcohol, p-dodecylaminobenzyl alcohol, p-tridecylaminobenzyl alcohol, p-pentadecylaminobenzyl alcohol, p-(14-methylpentadecyl)aminobenzyl alcohol, p-heptadecylaminobenzyl alcohol, p-octadecylaminobenzyl alcohol and p-nonadecylaminobenzyl alcohol.

Sources & evidence

ORD record
ord-b243fac4019d4d05b48c1413793dfc94
Source dataset
uspto-grants-1980_04
Patent number
US04198522

Reaction notes

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