4-(6-Hydroxyhexoxy)benzaldehyde → (E)-4-Carboxy-4'-[6-hydroxyhexyloxy]-stilbene

HRID 970251Notes

Reaction equation

HRID 970251 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[Br-].[C:18]([C:21]1[CH:46]=[CH:45][C:24]([CH2:25][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:23][CH:22]=1)([OH:20])=[O:19]>C(O)C>[C:18]([C:21]1[CH:46]=[CH:45][C:24](/[CH:25]=[CH:13]/[C:12]2[CH:15]=[CH:16][C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:10][CH:11]=2)=[CH:23][CH:22]=1)([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 150510824-(6-Hydroxyhexoxy)benzaldehydeHCID 22675580(4-Carboxybenzyl)triphenylphosphonium bromide

Product 1

HCID 59018740(E)-4-Carboxy-4'-[6-hydroxyhexyloxy]-stilbeneYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.43 g (62 mmole) of Li was dissolved in 180 ml of ethanol under a nitrogen atmosphere. Then 6.9 g (31 mmole) of 4-(6-hydroxyhexyloxy)-benzaldehyde (15) and 14.8 g (31 mmole) of (4-carboxy-benzyl)-triphenylphosphonium bromide (14) were added. The mixture was stirred for two hours at room temperature. The precipitate was collected on a filter and washed with 50 ml of ethanol. Then the solid was mixed with 1.5 ml of concentrated hydrochloric acid and 35 ml of ethanol. It was stirred for 30 min and the product was collected on a filter. After washing with 50 ml of ethanol and drying in a dessicator 4.1 g of the product were obtained (yield 38%).

Workup

  1. customThe precipitate was collected on
  2. filtrationa filter
  3. washwashed with 50 ml of ethanol
  4. additionThen the solid was mixed with 1.5 ml of concentrated hydrochloric acid and 35 ml of ethanol
  5. stirringIt was stirred for 30 min
  6. customthe product was collected on a filter
  7. washAfter washing with 50 ml of ethanol
  8. dry with materialdrying in a dessicator 4.1 g of the product
  9. customwere obtained (yield 38%)

Sources & evidence

ORD record
ord-b13c7fc6917c4f9c82d42f288b054d13
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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