Lithium hydroxide, monohydrate → 4-(Benzyloxy)-3-hydroxybenzoic acid

HRID 733333Notes

Reaction equation

HRID 733333 reaction equation
O.[OH-].[Li+].[CH2:4]([O:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([O:18]CC2C=CC=CC=2)=[O:17])=[CH:14][C:13]=1[OH:28])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.O1CCCC1>[CH2:4]([O:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[OH:28])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 54394841HCID 54394841, compound

Product 1

HCID 536525894-(Benzyloxy)-3-hydroxybenzoic acidYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium hydroxide hydrate (300 mg, 7.15 mmol) in water (15 cm3) was added dropwise to a stirred solution of benzyl 4-benzyloxy-3-hydroxybenzoate (1.177 g, 3.52 mmol) in tetrahydrofuran (35 cm3). The resulting emulsion was stirred overnight, by which time a clear, pale yellow solution had formed. More lithium hydroxide hydrate (300 mg, 7.15 mmol), water (25 cm3) and tetrahydrofuran (25 cm3) were added, and stirring was continued for 24 h. The tetrahydrofuran was removed under reduced pressure. Water (100 cm3) was added to the residual mixture, which was washed with diethyl ether (2×50 cm3), acidified to pH 1 with 5% HCl and extracted with dichloromethane (3×100 cm3). The combined extracts were washed with brine (50 cm3), dried (NaSO4) and evaporated to give 4-benzyloxy-3-hydroxybenzoic acid as a white solid (638 mg, 74%). The diethyl ether washings were extracted with 1 M potassium hydroxide (2×25 cm3). The combined extracts were acidified to pH 1 with 5% HCl and extracted with dichloromethane (3×100 cm3). The combined extracts were dried over MgSO4 and evaporated to give a further 119 mg of product (total yield 757 mg, 88%), m.p. 163-165° C.

Workup

  1. customhad formed
  2. stirringstirring
  3. waitwas continued for 24 h
  4. customThe tetrahydrofuran was removed under reduced pressure
  5. additionWater (100 cm3) was added to the residual mixture, which
  6. washwas washed with diethyl ether (2×50 cm3)
  7. extractionextracted with dichloromethane (3×100 cm3)
  8. washThe combined extracts were washed with brine (50 cm3)
  9. dry with materialdried (NaSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-afa3fceaeed845e5906b6996607e6231
Source dataset
uspto-grants-2009_09
Patent number
US07589170B1

Reaction notes

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