Hydrochloric Acid → Benzyl 5-hydroxymethyl-2-methoxybenzoate

HRID 1634522Notes

Reaction equation

HRID 1634522 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[C:7]([CH:18]=1)[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:2].[BH4-].[Na+].Cl>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[C:7]([CH:18]=1)[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22494335Benzyl 5-formyl-2-methoxybenzoate

Product 1

HCID 18678026Benzyl 5-hydroxymethyl-2-methoxybenzoateYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 5-formyl-2-methoxybenzoate (1.10 g, 4.07 mmol) and 30 ml of methanol were mixed and sodium borohydride (155 mg, 4.10 mmol) was added little by little under stirring and cooling with ice. After stirring for 2 hours under cooling with ice, the reaction mixture was poured into ice water and made acidic with 1 mol/l hydrochloric acid, which was extracted with ethyl acetate. The extract was washed with water and with brine, then dried over anhydrous sodium sulfate and concentrated to obtain 1.11 g (99%) of benzyl 5-hydroxymethyl-2-methoxybenzoate (without purifying further, this compound was used for the next reaction).

Workup

  1. temperaturecooling with ice
  2. stirringAfter stirring for 2 hours
  3. temperatureunder cooling with ice
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water and with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-41be7c8310f649f18a60aa11d78136ae
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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