Hydrochloric Acid → 4-[3-(Methoxymethyl)phenoxy]butyric acid, methyl ester

HRID 1248406Notes

Reaction equation

HRID 1248406 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13]C)=[O:11])=[O:2].Cl.[C:19]([BH3-])#N.[Na+].O>CO>[CH3:19][O:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 10466631Ethyl 4-(3-formylphenoxy)butanoate

Product 1

HCID 639857364-[3-(Methoxymethyl)phenoxy]butyric acid, methyl esterYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(3-formylphenoxy)butyric acid, ethyl ester (4.72 g) in methanol (25 ml) containing hydrogen chloride (0.35 g) was stirred for 12 hr. at room temperature, then cooled to 0°. Sodium cyanoborohydride (1.26 g) was added and after 30 min., iced water (200 ml) was added and the mixture extracted with ether (2×150 ml). Evaporation of the dried (MgSO4) ethereal extracts gave a pale yellow oil which was distilled (165°/0.8 mm) to give the title compound (3.8 g).

Workup

  1. extractionthe mixture extracted with ether (2×150 ml)
  2. customEvaporation of the
  3. dry with materialdried (MgSO4) ethereal extracts
  4. customgave a pale yellow oil which
  5. distillationwas distilled (165°/0.8 mm)

Sources & evidence

ORD record
ord-707e03744adc45dbbb601281329cf5cb
Source dataset
uspto-grants-1985_06
Patent number
US04524071

Reaction notes

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