Tetrahydrofuran → (3,5-Bis(docosyloxy)phenyl)methanol

HRID 573962Notes

Reaction equation

HRID 573962 reaction equation
[CH2:1]([O:23][C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH:33]=1)[C:27](OC)=[O:28])[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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>C(OCC)C>[CH2:35]([O:34][C:32]1[CH:31]=[C:26]([CH:25]=[C:24]([O:23][CH2:1][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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:33]=1)[CH2:27][OH:28])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 66651984Methyl 3,5-bis(docosyloxy)benzoate

Product 1

HCID 49844210(3,5-Bis(docosyloxy)phenyl)methanolYield 88.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

Under an argon atmosphere, methyl [3,5-bis(docosyloxy)]benzoate (2.03 g, 2.59 mmol) was dissolved in dehydrating tetrahydrofuran (50 mL) and, under ice-cooling, lithium aluminum hydride (148 mg, 3.93 mmol) was added, and the mixture was stirred at 40° C. for 1 hr. Ethyl acetate was added dropwise to decompose unreacted lithium aluminum hydride. Diethyl ether was added, and the mixture was washed with aqueous hydrochloric acid. The organic layer was concentrated under reduced pressure, methanol was added to the concentrated solution, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to give the title compound (1.73 g, 88.0%) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. washthe mixture was washed with aqueous hydrochloric acid
  3. concentrationThe organic layer was concentrated under reduced pressure, methanol
  4. additionwas added to the concentrated solution
  5. filtrationthe precipitated solid was collected by filtration
  6. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-81575cfebecf444cbad951efebe1d2df
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

Loading…