Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 17-Acetoxy-heptadecanol

HRID 910816Notes

Reaction equation

HRID 910816 reaction equation
[C:1]([O: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][O:22]C1CCCCO1)(=[O:3])[CH3:2].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO.CCOC(C)=O>[C:1]([O: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][OH:22])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57548717Tetrahydro-2-(17-acetoxyheptadecyloxy)-2H-pyran

Product 1

HCID 8662564017-Acetoxy-heptadecanolYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

THP ether 39 (1.207 g, 3.03 mmol) was dissolved in 95% EtOH (12 ml) and PPTS (76 mg, 0.3 mmol) was added. Reaction mixture was stirred at 55° C. for 4 h, cooled to room temperature and diluted with EtOAc. Mixture was washed with H2O three times, organic extract was dried over Na2SO4 and evaporated. Residue was chromatographed on silica gel to give 864 mg (91%) of 17-acetoxy-heptadecanol.

Workup

  1. customReaction mixture
  2. temperaturecooled to room temperature
  3. washMixture was washed with H2O three times
  4. extractionorganic extract
  5. dry with materialwas dried over Na2SO4
  6. customevaporated
  7. customResidue was chromatographed on silica gel

Sources & evidence

ORD record
ord-ad9debc360de42ee8c4eac8307b0ae29
Source dataset
uspto-grants-2011_09
Patent number
US08022235B2

Reaction notes

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