Hydrochloric Acid → Methyl 2-(4-hydroxymethylphenoxy)acetate

HRID 2405182Notes

Reaction equation

HRID 2405182 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=1.[B-].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 758214Methyl 2-(4-formylphenoxy)acetateHCID 22959485Vertellus

Product 1

HCID 690034Methyl 2-(4-hydroxymethylphenoxy)acetateYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-Formylphenoxy)acetic acid methyl ester 68 (160 grams, 825 mmol) in methanol (800 mL) at 0° C. was added Sodium borohydrate (18 grams, 476 mmol) in small portions, further stirred at 0° C. for 2 hours and poured on to ice water (1500 mL). The pH of mixture was adjusted to 2 with concentrated hydrochloric acid. Crude 69 was extracted into chloroform, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane:ethyl acetate (7:3) to give 69 (100 grams, 62%) as white powder

Workup

  1. extractionCrude 69 was extracted into chloroform
  2. dry with materialdried over Na2SO4
  3. distillationdistilled
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c44e5af7ea9f42fb81372288e1eb3576
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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