Borane → [4-(Tridecyloxy)phenyl]methanol

HRID 2052489Notes

Reaction equation

HRID 2052489 reaction equation
B.[CH2:2]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>O1CCCC1>[CH2:2]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:23][CH:24]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 6331BoraneHCID 202434544-(Tridecyloxy)benzoic acid

Product 1

HCID 13079696[4-(Tridecyloxy)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 ml. of 1.0 M borane in tetrahydrofuran, chilled in an ice bath is added dropwise over 30 minutes 32.0 g. of p-tridecyloxybenzoic acid in 450 ml. of tetrahydrofuran. After 22 hours at room temperature, the mixture is poured onto ice. After the ice melts, the solid is filtered and washed with water to give white crystals, m.p. 72°-75° C. Recrystallization from ethanol gives white crystals, m.p. 74°-75° C.

Workup

  1. additionis added dropwise over 30 minutes 32.0 g
  2. additionthe mixture is poured onto ice
  3. filtrationthe solid is filtered
  4. washwashed with water
  5. customto give white crystals, m.p. 72°-75° C
  6. customRecrystallization from ethanol
  7. customgives white crystals, m.p. 74°-75° C.

Sources & evidence

ORD record
ord-f2e53cf0879749c7910cf8ba228c9ebf
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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