3-(4-Hydroxymethylphenoxy)propionic acid → Benzenemethanol, 4-(3-hydroxypropoxy)-

HRID 2115215Notes

Reaction equation

HRID 2115215 reaction equation
[OH:1][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][CH2:9][C:10](O)=[O:11])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:1][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7363043-(4-Hydroxymethylphenoxy)propionic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 11458058Benzenemethanol, 4-(3-hydroxypropoxy)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(4-hydroxymethylphenoxy)propionic acid (4.00 g, 20.40 mmol) in THF (20 mL) is added a solution of LiAlH4 (10 mL, 1 M in THF). The mixture becomes warm and is diluted with THF (20 mL) before it is refluxed. After 1 and 2 h two further portions of LiAlH4 (2×10 mL, 1 M in THF) are added. The mixture is refluxed overnight, cooled to rt and carefully quenched by the addtion of water (1.2 g), 15% aq. NaOH (1.2 g) and water (3.2 g). The white precipitate is filtered off, and the filtrate is evaporated and dried to give 3-(4-hydroxymethyl-phenoxy)-propan-1-ol. 1H NMR (D6-DMSO): δ 7.21-7.15 (m, 2H), 6.86-6.81 (m, 2H), 5.00 (t, J=5.9 Hz, 1H), 4.51 (t, J=5.3 Hz, 1H), 4.39 (d, J=5.3 Hz, 2H), 3.99 (t, J=6.4 Hz, 2H), 3.57-3.50 (m, 2H), 1.83 (p, J 0 6.4 Hz, 2H).

Workup

  1. temperatureThe mixture becomes warm
  2. temperatureis refluxed
  3. temperatureThe mixture is refluxed overnight
  4. customcarefully quenched by the addtion of water (1.2 g), 15% aq. NaOH (1.2 g) and water (3.2 g)
  5. filtrationThe white precipitate is filtered off
  6. customthe filtrate is evaporated
  7. customdried

Sources & evidence

ORD record
ord-76869529f2fa49c0b42c52203c9719a0
Source dataset
uspto-grants-2008_10
Patent number
US07435828B2

Reaction notes

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