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

HRID 987343

반응식

HRID 987343 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-322935217942452cae26b1a4d8ddfafd
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630128B1

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