4-Hydroxybenzaldehyde → 4-(16-Hydroxy-hexadecyloxy)-benzaldehyde

HRID 987343

反応式

HRID 987343 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH:10][CH2:11][CH2:12][CH2:13][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]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[OH:10][CH2:11][CH2:12][CH2:13][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][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 821841,16-HexadecanediolHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 229875534-(16-Hydroxy-hexadecyloxy)-benzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 4-hydroxy-benzaldehyde (0.24 g, 2mmol) and 1,16-dihydroxyhexadecane (0.51 g, 2 mmol), triphenylphosphine (0.53 g, 2 mmol) in dry THF (20 ml) at −15° C. under an argon atmosphere was added a solution of diisopropylazodicarboxylate (0.4 g, 2 mmol) in dry THF (7.5 ml) over a period of 40 minutes. The mixture was allowed to warm to room temperature overnight. The solvent was removed under reduced pressure, diethyl ether was added and the white solid formed was removed by filtration. The filtrate was evaporated to dryness and the residue purified by chromatography on a column of silica gel which was, eluted with petroleum ether (b.p. 40-60° C.):tetrahydrofuran (THF) (10:1 by volume) to yield the title compound which was used directly without further purification.

後処理

  1. customThe solvent was removed under reduced pressure, diethyl ether
  2. additionwas added
  3. customthe white solid formed
  4. customwas removed by filtration
  5. customThe filtrate was evaporated to dryness
  6. customthe residue purified by chromatography on a column of silica gel which
  7. washeluted with petroleum ether (b.p. 40-60° C.)

出典と根拠

ORDレコード
ord-322935217942452cae26b1a4d8ddfafd
出典データセット
uspto-grants-2003_10
特許番号
US06630128B1

関連ノート

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