11-Phenoxyundecanoic acid → 11-Phenoxy-1-undecanol

HRID 2051905Notes

Reaction equation

HRID 2051905 reaction equation
B#B.[O:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[O:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 8159711-Phenoxyundecanoic acidHCID 6328200Diboron

Product 1

HCID 1157250211-Phenoxy-1-undecanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 ml of 1M diborane in tetrahydrofuran under nitrogen chilled in an ice bath is added dropwise 13.92 g of 11-phenoxyundecanoic acid in 50 ml of tetrahydrofuran over 30 minutes. The solution is allowed to stand at room temperature for 19 hours and is poured onto ice. After standing, the mixture is filtered and the solid washed with water to give white crystals, mp 56°-58° C. A sample on recrystallization from ethanol gives white crystals, mp 56.5°-57.5° C.

Workup

  1. additionis poured onto ice
  2. filtrationthe mixture is filtered
  3. washthe solid washed with water
  4. customto give white crystals, mp 56°-58° C
  5. customA sample on recrystallization from ethanol
  6. customgives white crystals, mp 56.5°-57.5° C.

Sources & evidence

ORD record
ord-398688844dd443709b9e67856e538ff6
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

Loading…