4-Hydroxybenzaldehyde → 4-(3,4,5-Tris-octadecyloxy-cyclohexylmethoxy)-benzaldehyde

HRID 1754827Notes

Reaction equation

HRID 1754827 reaction equation
[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][OH:65])[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O[C:67]1[CH:74]=[CH:73][C:70]([CH:71]=[O:72])=[CH:69][CH:68]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][O:65][C:67]2[CH:74]=[CH:73][C:70]([CH:71]=[O:72])=[CH:69][CH:68]=2)[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1264-Hydroxybenzaldehyde2×HCID 11776Triphenylphosphine3×HCID 866457853,4,5-Tris(octadecyloxy)cyclohexylmethyl alcohol

Product 1

HCID 595103544-(3,4,5-Tris-octadecyloxy-cyclohexylmethoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3,4,5-Tris-octadecyloxy-cyclohexyl)-methanol (283 mg, 308 μmol), 4-hydroxy-benzaldehyde (56 mg, 459 μmol), triphenylphosphine (121 mg, 461 μmol) dissolved in dehydrated THF (5.5 mL), DIED (93.3 μL, 472 μmol) was added and the mixture was stirred for 40 min. 4-Hydroxy-benzaldehyde, triphenylphosphine and DIED (each 153 μmol) were added and the mixture was stirred overnight. Triphenylphosphine and DIED (each 306 μmol) were added and the mixture was stirred for 2.5 hr. THF was evaporated, and 90% aqueous acetonitrile (6 ml) was added to the residue to allow crystallization. The crystals were collected by filtration and thoroughly washed with acetonitrile to give crude crystals of 4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-benzaldehyde. The crude crystals were purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give the object compound (130 mg, 127 μmol, 41%).

Workup

  1. additionDIED (93.3 μL, 472 μmol) was added
  2. additionwere added
  3. stirringthe mixture was stirred overnight
  4. additionwere added
  5. stirringthe mixture was stirred for 2.5 hr
  6. customTHF was evaporated
  7. addition90% aqueous acetonitrile (6 ml) was added to the residue
  8. customcrystallization
  9. filtrationThe crystals were collected by filtration
  10. washthoroughly washed with acetonitrile

Sources & evidence

ORD record
ord-d16bf704eef14652962ea2dfd2f2d575
Source dataset
uspto-grants-2015_10
Patent number
US09169187B2

Reaction notes

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