Hydrochloric Acid → 4-(Hexadecylamino)benzoic acid

HRID 1659628ノート

反応式

HRID 1659628 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[Cl-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.Cl>C(O)C>[CH2:29]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 9890573Phosphonium, tributylhexadecyl-, chloride

生成物 1

HCID 472634-(Hexadecylamino)benzoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

27.4 g (0.2 mol) of 4-aminobenzoic acid, 11.2 g of KOH, 64 g (0.21 mol) of 1-bromohexadecane and 4.64 g (10 mmol) of hexadecyltributylphosphonium chloride were suspended in 250 ml of ethanol (96%) and the reaction mixture was stirred for 12 hours at reflux temperature. While the solution was still hot, there were added, drop by drop, 80 ml of conc. HCl and the reaction mixture was left to cool down to ambient temperature. Thereupon the precipitated product was separated on a suction filter, washed with water and dried. After the crystallization of the crude product from benzene, there was obtained the 4-(n-hexadecylamino)-benzoic acid, m.p. 107°-107° C., complete m.p. 122°-126° C., which could be optionally converted into its sodium salt.

後処理

  1. temperatureat reflux temperature
  2. additionthere were added
  3. customThereupon the precipitated product was separated on a suction
  4. filtrationfilter
  5. washwashed with water
  6. customdried
  7. customAfter the crystallization of the crude product from benzene

出典と根拠

ORDレコード
ord-753192602afc4e6bbffd5580619d74ca
出典データセット
uspto-grants-1981_12
特許番号
US04304929

反応ノート

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