Water → 2-(Hydroxymethyl)-7-methoxy-9H-xanthen-9-OL

HRID 436000

Reaction equation

HRID 436000 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:22]=[C:21]2[C:12]([O:13][C:14]3[CH:15]=[CH:16][C:17]([C:24](OCC)=[O:25])=[CH:18][C:19]=3[C:20]2=[O:23])=[CH:11][CH:10]=1.O.[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[OH:23][CH:20]1[C:19]2[CH:18]=[C:17]([CH2:24][OH:25])[CH:16]=[CH:15][C:14]=2[O:13][C:12]2[C:21]1=[CH:22][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 21455094Ethyl 7-methoxy-9-oxoxanthene-2-carboxylate

Product 1

HCID 214550952-(Hydroxymethyl)-7-methoxy-9H-xanthen-9-OLYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (500 mg) was added to a stirred solution of ethyl 7-methoxy-9-oxoxanthene-2-carboxylate (1g) in THF (100 ml). The reaction mixture was stirred at room temperature under nitrogen for 5 hours. Water and MgSO4 were added. The inorganic solids were filtered off and washed with ethyl acetate. The filtrate and washings were combined and evaporated to give the crude product. Recrystallization from ethyl acetate gave white crystals (0.82 g, 84%), mp. 142°-143°.

Workup

  1. filtrationThe inorganic solids were filtered off
  2. washwashed with ethyl acetate
  3. customevaporated
  4. customto give the crude product
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-67a38b1b31974630bd45356f0540d6db
Source dataset
uspto-grants-1977_02
Patent number
US04007205

Linked notes

Loading…