Methanol → HCID 21500850, compound

HRID 1658555Notes

Reaction equation

HRID 1658555 reaction equation
[C:1]([C:4]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:5]=1[O:6][C:7]1[CH:8]=[CH:9][C:10]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][C:12]=1[CH2:13]2)(=[O:3])[CH3:2].CO.[BH4-].[Na+].O>C(O)(=O)C>[OH:3][CH:1]([C:4]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:5]=1[O:6][C:7]1[CH:8]=[CH:9][C:10]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][C:12]=1[CH2:13]2)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 4311764Sodium borohydrideHCID 21500551HCID 21500551, compound

Product 1

HCID 21500850HCID 21500850, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6 g. of methyl 5-acetyl-7-methylxanthene-2-carboxylate in 500 ml. of absolute methanol are added 1.1 g. of sodium borohydride in 50 ml. of water at a temperature of from 25° to 30°C with stirring, over a period of about 30 minutes. After 15 minutes under these conditions, 400 ml. of water and 20 ml. of acetic acid are added and the resultant mixture is stripped of solvent. The resultant mixture is extracted with methylene chloride and washed with bicarbonate and water. The washed extracts are concentrated to give methyl 5-(1-hydroxyethyl)-7-methylxanthene-2-carboxylate.

Workup

  1. extractionThe resultant mixture is extracted with methylene chloride
  2. washwashed with bicarbonate and water
  3. concentrationThe washed extracts are concentrated

Sources & evidence

ORD record
ord-f4171593c4bc436c91d2acc168cce283
Source dataset
uspto-grants-1976_06
Patent number
US03965115

Reaction notes

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